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[ CAS No. 852138-89-7 ] {[proInfo.proName]}

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Chemical Structure| 852138-89-7
Chemical Structure| 852138-89-7
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Product Details of [ 852138-89-7 ]

CAS No. :852138-89-7 MDL No. :MFCD14582983
Formula : C12H6Br2I2 Boiling Point : -
Linear Structure Formula :- InChI Key :JPXBIAWPJOGFCF-UHFFFAOYSA-N
M.W : 563.79 Pubchem ID :57892321
Synonyms :

Calculated chemistry of [ 852138-89-7 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 92.71
TPSA : 0.0 ?2

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.62
Log Po/w (XLOGP3) : 6.23
Log Po/w (WLOGP) : 6.09
Log Po/w (MLOGP) : 6.7
Log Po/w (SILICOS-IT) : 6.75
Consensus Log Po/w : 5.88

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 0.0
Egan : 1.0
Muegge : 2.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -7.75
Solubility : 0.00001 mg/ml ; 0.0000000178 mol/l
Class : Poorly soluble
Log S (Ali) : -6.02
Solubility : 0.000543 mg/ml ; 0.000000964 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -8.26
Solubility : 0.00000308 mg/ml ; 0.0000000055 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.29

Safety of [ 852138-89-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 852138-89-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 852138-89-7 ]

[ 852138-89-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 852138-89-7 ]
  • [ 18204-93-8 ]
  • [ 852138-90-0 ]
YieldReaction ConditionsOperation in experiment
53% t-BuLi (15.3 mL, 0.0261 mol, 1.7 M in pentane) was slowly added to a solution of 4,4?- dibromo-2,2?-diiodobiphenyl (compound 1, 3.50 g, 6.21 mmol) in dry THF (40 mL), over 30 mins, at 95 O (hexanes/liquid nitrogen) under a nitrogen inert atmosphere. The reaction mixture was stirred for a further one hour at 95 c and dichlorodihexylsilane (3.34 g, 0.0124mol) was subsequently added and was stirred at room temperature overnight. Water (50 mL) was added and the product was extracted into diethylether (3 x 50 mL), the ethereal extracts washed with water (150 mL), dried (Mg504), filtered and concentrated under reduced pressure. The crude product was purified by gravity column chromatography (wet loaded, silica gel, hexanes) to yield compound 2 as a colourless oil (1.67 g, 53%).1H NMR (400 MHz, CDCI3): O (ppm) 0.84 (6 H, t, J = 6.8 Hz, OH3), 0.91-0.95 (4 H, m, OH2),1.18-1.33 (16 H, m, OH2), 7.53 (2 H, dd, J = 2.0 and 8.0 Hz, Ar-H), 7.63 (2 H, d, J = 8.4 Hz, Ar-H), 7.68 (2 H, d, J = 2.0 Hz, Ar-H).
Under the protection of argon, 6.00 g of 4,4?-dibromo-2,2?-diiodo biphenyl was dissolved in 100 mL of THF, cooled to -100 C., then to the solution 42.55 mL of methyl lithium solution (methyl lithium/n-hexane in 1.0 M) was added dropwise. After 12 hours of reaction, 5.70 g dihexyl dichlorosilane was added, and the reaction was continued for another 48 hours, the reaction was completed, then a water was added, and the mixture was extracted with diethyl ether, dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product, MALDI-TOF-MS (m/z): 508.4 (M+);
Under the protection of argon, 6.00 g of 4, 4'-dibromo-2, 2'-diiodo biphenyl was dissolved in 100 mL of THF, cooled to -100 C, then to the solution 42.55 mL of methyl lithium solution (methyl lithium/n-hexane in 1.0 M) was added dropwise. After 12 hours of reaction, 5.70 g dihexyl dichlorosilane was added, and the reaction was continued for another 48 hours, the reaction was completed, then a water was added, and the mixture was extracted with diethyl ether, dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product, MALDI-TOF-MS (m/z): 508.4 (M +);
  • 2
  • [ 136630-36-9 ]
  • [ 852138-89-7 ]
YieldReaction ConditionsOperation in experiment
29% A 17% (w/w) HCl aqueous solution (85mL) at 0C was added to the compound containing (Beta-3) (8 ·5g, 25mmol) of Round-bottomed flask, and to this was added NaNO2 (NaNO2 solution [NaNO24.3g (62mmol) + water (15mL)] was added . The mixture was stirred for 30 minutes, and this was added an aqueous solution of KI [KI 41.5g (250_mmol) + water (15mL) ]. the mixture was stirred at room temperature for 1 hour, at 60 C and stirred for 3 hours. K0H with a saturated solution and extracted with ethyl acetate and washed with saturated Na2SO3 (V Dr Di, the residue was purified by column chromatography to give compound B-4 (4g, 29%).
29% At a temperature of about 0 C., 85 mL of a 17% (w/w) HCl aqueous solution and a NaNO2 aqueous solution including 4.3 g (62 mmol) of NaNO2 and 15 mL of water were added to a round-bottom flask containing 8.5 g (25 mmol) of Intermediate 4-2. The resulting mixture was stirred for about 30 minutes, and a KI aqueous solution including 41.5 g (250 mmol) of KI and 15 mL of water was added thereto, followed by stirring for about 1 hour at room temperature and then stirring at a temperature of about 60 C. for about 3 hours. A saturated KOH solvent was used to neutralize the resulting mixture. An organic layer was extracted therefrom using ethyl acetate, washed with saturated Na2SO3, and purified through silica gel chromatography, thereby producing 4 g (yield: 29%) of Intermediate 4-3.
29% To a round bottom flask containing 8.5 g (25 mmol) of the compound B-3 at 0 C was added 85 mL of 17% (w/w) aqueous HCl solution and an aqueous solution of NaNO2 [4.3 g (62 mmol) of NaNO2 + 15 mL of water] was added. Stirred for 30 minutes and KI aqueous solution [KI 41.5 g (250 mmol) + water 15 mL] was added. Stirred at room temperature for 1 hour and stirred at 60 C for 3 hours. The reaction mixture was neutralized with saturated KOH solvent, extracted with ethyl acetate, washed with saturated Na2SO3 and then purified by silica column to obtain 4 g (29%) of compound B-4.
29.1% 87.7 g (0.256 mol) of 4,4'-dibromo-2,2'-diaminobiphenyl,380 mL of 12 M HCl, and 380 mL of water.The temperature of the reactor was lowered to 0 C.Sodium nitrite (44.2 g, 0.641 mol) was dissolved in 220 mL of water, slowly added dropwise to the reactor,When the addition was complete, the mixture was stirred at the same temperature for 1 hour for 1 hour.Potassium iodide was dissolved in 850 mL of water and slowly added dropwise. When the dropwise addition was completed, the solution was stirred at room temperature for 1 hour.The temperature of the reactor was raised to 60 DEG C and stirred for 3 hours.When the reaction was complete, the mixture was cooled to room temperature and extracted with Ethylacetate to separate the organic layer.The separated organic layer was dried over anhydrous, dried and then subjected to column chromatography using hexane as a developing solvent to obtain 42.1 g (yield: 29.1%) of 4,4'-dibromo-2,2'-diiodobiphenyl.
29.1% 87.7 g (0.256 mol) of 4,4'-Dibromo-2,2'-diaminobiphenyl, 380 mL of 12 M HCl, and 380 mL of water were added thereto. The temperature of the reactor was lowered to 0 C.Sodiumnitrite 44.2 g (0.641 mol) was dissolved in 220 mL of water and slowly added dropwise to the reactor, and when the dropwise addition was completed, the mixture was stirred for 1 hour at the same temperature for 1 hour.Potassium iodide was dissolved in 850 mL of water and slowly added dropwise, and when the addition was completed, the mixture was stirred at room temperature for 1 hour.And the temperature of the reactor was heated up to 60 degreeC and stirred for 3 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with ethylacetate to separate the organic layer. The organic layer was dried over anhydrous and dried, and then separated by column chromatography using hexane as a developing solvent, to obtain 42.1g (29.1%) of 4,4'-dibromo-2,2'-diodiobiphenyl.
29.1% 87.7 g (0.256 mol) of 4,4'-Dibromo-2,2'-diaminobiphenyl, 380 mL of 12 M HCl, and 380 mL of water were added thereto. The temperature of the reactor was lowered to 0 C.Dissolve 44.2 g (0.641 mol) of sodium nitrite in 220 mL of water and slowly add it to the reactor,When the dropwise addition was completed, the mixture was stirred for 1 hour at the same temperature.Potassium iodide was dissolved in 850 mL of water and slowly added dropwise, and when the addition was completed, the mixture was stirred at room temperature for 1 hour. And the temperature of the reactor was heated up to 60 degreeC and stirred for 3 hours.After the reaction was completed, the reaction mixture was cooled to room temperature and extracted with Ethylacetate to separate the organic layer.The organic layer was dried over anhydrous and dried, and then separated by column chromatography using hexane as a developing solvent, to obtain 42.1g (29.1%) of 4,4'-dibromo-2,2'-diodiobiphenyl.
29% [Intermediate 5-b] (87.7 g, 0.256 mol) synthesized in [Scheme 5-2] was added to 380 mL of 12 M hydrochloric acid and 380 mL of distilled water.Put the sodium nitrite (44.2 g, 0.641 mol) at 0 was dissolved in 220 mL of distilled water, slowly added dropwise and stirred for 1 hour. Potassium iodide was dissolved in 850 mL of distilled water, slowly added dropwise, and stirred at room temperature for 1 hour. The temperature was raised to 60 C. and stirred for 3 hours. Extracted with ethyl acetate and separated by column chromatography to obtain [Intermediate 5-c] 42.1 g (yield 29%).
29.1% 4,4'-dibromo-2,2'-diaminobiphenyl87.7 g (0.256 mol), 380 mL 12 M HCl,380 mL of water was added. The temperature of the reactor was lowered to 0 C.44.2 g (0.641 mol) of sodiumnitrite was dissolved in 220 mL of water and slowly added dropwise to the reactor,When the dropwise addition was completed, the mixture was stirred for 1 hour at the same temperature for 1 hour. Potassium iodide was dissolved in 850 mL of water and slowly added dropwise.When the dropwise addition was completed, the mixture was stirred at room temperature for 1 hour. And the temperature of the reactor was raised to 60 C. and stirred for 3 hours.When the reaction was completed, the mixture was lowered to room temperature and extracted using Ethylacetate to separate the organic layer.The separated organic layer was dried by anhydrous treatment, and then separated by column chromatography using hexane as a developing solvent.42.1 g (29.1%) of 4,4'-dibromo-2,2'-diiodobiphenyl was obtained.
27% Step ^ - Preparation of Compound Int-43bTo a stirred suspension of 2,2'-diamino-4,4'-dibromobiphenyl Int-43a (11.2 g, 33 mmol) (prepared from J. Am. Chem. Soc. 2005, 127, 7662) in cone. HC1 (50 mL)/water (50 mL) at 0 C was added a 50% soln of NaN02 in water (30 mL, 73 mmol) over 30 minutes while maintaining the temperature <5 C. The mixture was allowed to stir for an additional 30 minutes whereupon a soln of KI (54 g, 0.33 mol) in water (120 mL) was added dropwise over 1 h. The resulting mixture was heated to 60 C and was allowed to stir for 5h. The mixture was cooled to room temperature and was filtered. The resultant solid was washed with EtOAc (~ 500 mL) and the resultant filtrate was washed with brine (2 x 50 mL), dried (Na2S04), filtered, and concentrated in vacuo. The crude product was purified using flash chromatography using 100% hexanes to provide 5.1 g (27%) of compound Int-43b as a colorless oil.
25% With toluene-4-sulfonic acid; potassium iodide; sodium nitrite; In water; acetonitrile; at 20℃;Inert atmosphere; (3) The compound 3 (7.16 g, 20 mmol) and p-toluenesulfonic acid (17.18 g, 90.4 mmol) were dissolved in 200 mL of acetonitrile, stirred at 0 C for half an hour, and sodium nitrite (4.14, 1) and potassium iodide (12.45 g, 75 mmol) were dissolved in 40 mL of water and added dropwise to the reaction flask with a constant pressure dropping funnel, which was then allowed to warm to room temperature and allowed to react overnight. After completion of the reaction, the saturated sodium thiosulfate solution was added to the reaction solution and the resulting iodine was extracted and extracted with methylene chloride. The organic phase was collected and dried over anhydrous sodium sulfate. The product was purified by silica gel chromatography using petroleum ether as eluent The residue was purified by column chromatography and dried in vacuo to give a white solid 4 in a yield of 25%
23% 4,4'-Dibromo-1,1'-biphenyl-2,2'-diamine(16g, 46.8 mmol) dissolved in a mixture of 56 mL hydrochloric acid and 64 mL water.Stir under ice bath. after that,An aqueous solution of 40 mL of sodium nitrite (8 g, 116 mmol) was slowly added dropwise to the reaction solution, and the temperature was constant at about 0 C during the dropwise addition. After the addition is completed,The mixture was stirred for 30 minutes, and an aqueous solution of potassium iodide (77 g dissolved in 150 mL of water) was added dropwise to the reaction solution at -5 C.After the reaction at room temperature for 1 hour, the temperature was raised to 60 C for 3 hours.The solution turned dark brown. After the reaction is completed, the reaction solution is suction filtered.Purified by column chromatography (silica gel, n-hexane) to give a white solid(6.07g, 23%).
18% To a mixture of 4,4'-Dibromobiphenyl-2,2'-diamine (1.8 g, 4.5 mmol) and 8 N HCl aqueous solution (35 mL), an aqueous solution of sodium nitrite (0.7 g, 10.1 mmol) was added dropwise at 0 C. After stirring for 30 min, a solution of KI (1.6 g, 9.6 mmol) in water (5 ml) was slowly added during 5 min. Then, the mixture was warmed up to room temperature for 1 h. The mixture was extracted with CH2Cl2 (3×30 mL). The organic phase was washed with saturated sodium thiosulfate solutionan and water, and dried over anhydrous Na2SO4. After concentrated under vacuum, the crude product was purified by column chromatography silica gel with petroleum ether to get white solid (0.5 g, 18%). 1H NMR (400 MHz, CDCl3): 8.09 (d, J = 2.0 Hz, 2H), 7.55 (dd, J = 8.4, 2.0 Hz, 2H), 7.03 (d, J = 8.0 Hz, 2H).
To 36% hydrochloric acid/water (75 ml/85 ml) was added 21.3 g of the compound (10-c), and to this, an aqueous NaNO2 solution (NaNO2 10.7 g/water 55 ml) was added dropwise at 5C. The resulting mixture was stirred at 5C for 30 minutes, and then an aqueous KI solution (KI 104 g/water 200 ml) was added dropwise and the resulting mixture was stirred at 5C for 1 hour, at room temperature for 1 hour and at 60C for 3 hours. A solid fraction produced was collected by filtration and purified by column chromatography (filler: silica gel, eluent: hexane) to obtain 4.27 g of compound (10-d).

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[2]Journal of Materials Chemistry A,2016,vol. 4,p. 8750 - 8754
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[5]Organic electronics,2018,vol. 59,p. 77 - 83
[6]Patent: CN103819455,2016,B .Location in patent: Paragraph 0067; 0072; 0073
[7]Patent: US2017/69856,2017,A1 .Location in patent: Paragraph 0223; 0226
[8]Patent: KR2015/34146,2015,A .Location in patent: Paragraph 0059; 0064; 0065
[9]Patent: KR101964677,2019,B1 .Location in patent: Paragraph 0207; 0208; 0243-0247
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[11]Patent: KR102002020,2019,B1 .Location in patent: Paragraph 0217; 0218; 0252-0256
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  • 3
  • [ 852138-89-7 ]
  • [ 18416-07-4 ]
  • [ 891182-24-4 ]
YieldReaction ConditionsOperation in experiment
40% 4,4'-Dibromo-2,2'-diiodobiphenyl (2.8 g, 4.9 mmol) was dissolved in 90 mL of anhydrous tetrahydrofuran, and a solution of 2.5 M n-butyllithium in n-hexane was added at -78 C.(7.8mL, 19.5mmol), heat preservation reaction for 1 hour,Dioctyldichlorosilane (1.8 g, 5.4 mmol) was then added rapidly.The reaction was incubated for 30 minutes, after which the reaction solution was allowed to warm to room temperature overnight.After the reaction is completed, the reaction is quenched with water, extracted, and the organic phase is washed with brine.Dry and purify by column chromatography to give a white solid (1,1g, 40%)
In 85 ml of tetrahydrofuran (produced by Wako Pure Chemical Industries, Ltd.) was dissolved 4.27 g of the compound (10-d), and the resulting solution was cooled to -80C. After adding 19 ml of a 1.6 M hexane solution of n-butyl lithium (produced by Wako Pure Chemical Industries, Ltd.) over 1 hour, the resulting mixture was stirred under a nitrogen atmosphere at -80C for 30 minutes. 5.2 ml of dichlorodioctylsilane (produced by Wako Pure Chemical Industries, Ltd.) was added, and the temperature of the resulting mixture was raised to room temperature and the mixture was stirred under a nitrogen atmosphere for one day. To the resulting solution was added 50 ml of water and the solvent was distilled off. After adding 150 ml of diethyl ether, an organic layer was fractionated, washed with 400 ml of water, and then dried with magnesium sulfate. The resulting solution was purified by column chromatography (filler: silica gel, eluent: hexane) to obtain 2.49 g of compound (10-e).
  • 8
  • [ 852138-89-7 ]
  • 9,9-dichloro-2,7-dibromo-9-silafluorene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; tetrachlorosilane; In tetrahydrofuran; hexane; at -100℃; for 6.33333h; The intermediate X-1 (0.70 g, 1.24 mmol) was weighed into a well-dried round bottom flask.Add 100 mL of anhydrous tetrahydrofuran and the temperature is lowered to -100 C.Butyllithium (2.2 mL, 5.5 mmol, 2.5 M in hexane) was added dropwise, the dropping time was continued for 20 min, and the reaction was maintained at -100 C for 2 h.One-time addition of silicon tetrachloride (1.5 mL, 12.4 mmol), after 4 h at low temperature,The temperature was naturally raised, and the reaction was carried out overnight, and unreacted silicon tetrachloride and a solvent tetrahydrofuran were removed by distillation under reduced pressure.Accurately weigh 2,2'-dibromo-1,1'-biphenyl (0.39 g, 1.24 mmol) in a well-dried round bottom flask.After adding 40 mL of anhydrous diethyl ether, it was placed in a dry ice-acetone bath, n-butyllithium (1.1 mL, 2.48 mmol, 2.5M hexane) was added dropwise, and the mixture was returned to room temperature overnight.At -78 C,The system was introduced into the reaction bottle of the first step, returned to room temperature, and reacted for 8 hours;Add 40 mL of a saturated aqueous solution of ammonium chloride, extract with diethyl ether, dry, evaporate the solvent, and use petroleum ether as a mobile phase to carry out column chromatography;A white solid X-3 (0.2 g, yield 35%) was obtained.
  • 9
  • [ 852138-89-7 ]
  • [ 644-97-3 ]
  • [ 1356238-89-5 ]
  • 10
  • [ 852138-89-7 ]
  • [ 18416-07-4 ]
  • [ 958293-23-7 ]
  • 11
  • [ 852138-89-7 ]
  • [ 75-78-5 ]
  • [ 1228595-79-6 ]
YieldReaction ConditionsOperation in experiment
76% comprising the compound B-4 (4g, 7. Lmmol) A round bottom flask filled with argon, and to this 30mL of THF was added . The mixture was cooled to -78C. Was slowly added n-BuLi (in hexane 2. 5M, 6. 2mL, 15. 6mmol) and stirred for 1 hour. to this dichlorodimethylsilane (2. 0g, 15. 6mmol) was added , and slowly heated to reflux for 12 hours at room temperature. After extraction with EA and washed with water, drying the resulting organic layer to give Compound B-5 (2g, 76%) was purified by column chromatography on silica
76% A round bottom flask containing 4 g (7.1 mmol) of compound B-4 was charged with argon gas, 30 mL of THF was added, and the solution was cooled to -78 C. 6.2 mL (15.6 mmol) of n-BuLi (2.5 M in hexane) was added slowly and stirred for 1 hour. 2.0 g (15.6 mmol) of dichlorodimethylsilane was added and the temperature was slowly raised to room temperature while stirring for 12 hours, followed by extraction with EA and washing with water. The obtained organic layer was dried and purified by silica column to obtain 2 g (76%) of Compound B-5.
76% A round-bottom flask containing 4 g (7.1 mmol) of Intermediate 4-3 was filled with argon gas and 30 mL of tetrahydrofuran (THF). The resulting mixture was then cooled to a temperature of about -78 C. 6.2 mL (15.6 mmol) of n-BuLi (2.5 molar (M) in hexane) was slowly added thereto, and the resulting solution was stirred for about 1 hour. 2.0 g (15.6 mmol) of dichlorodimethyl silane was added thereto. The resulting solution was stirred for about 12 hours and the temperature was allowed to slowly come to room temperature. An organic layer was extracted using ethyl acetate and washed with water. The obtained organic layer was dried and purified through silica gel chromatography, thereby producing 2 g (yield: 76%) of Intermediate 4-4.
56.36% To a solution of <strong>[852138-89-7]4,4'-dibromo-2,2'-diiodo-1,1'-biphenyl</strong> (10.0 g, 17.74 mmol, 1.00 eq) in 70 ml of tetrahydrofuranAfter dissolution, 2.5 M n-Butyl lithium in hexane (35.47 ml, 56.76 mmol, 3.2 eq) was slowly added at 100 C.After 5 hours of reaction, dichlorodimethylsilane (2.4 g, 18.62 mmol, 1.05 eq) was slowly added.After 24 hours of reaction, the reaction mixture was distilled under reduced pressure to remove the solvent. Distilled water (100 ml × 3) and dichloromethane were added to the reaction mixture to remove water with MgSO 4. After filtering and drying, 3.68 g of the target compound (yield: 56.36%) was obtained.
50% Under nitrogen protection, in a 500mL three-necked bottle containing magnets,Adding 4,4-dibromo-2,2-diiodobiphenyl as raw material(52g, 92.8mmol, 1eq), dissolved in 300mL of tetrahydrofuran,The reaction solution was cooled to a low temperature of -78 C, then 2.5 M n-butyllithium / n-hexane solution (142 mL, 185.6 mmol, 2 eq) was added dropwise, and stirred at a constant temperature for 1 h.Then dichlorodimethylsilane (35 g, 185.6 mmol, 2 eq) was added dropwise, and stirred at constant temperature for 1 h.Then it was stirred at room temperature for 12 h.After the end of the reaction, it was extracted three times with EA/H 2 O.The crude product was purified by silica column chromatography.White solid17 g, yield 50%.
50% Under the protection of nitrogen, in a 500mL three-necked bottle with magnets,Add the starting material 4,4-dibromo-2,2-diiodobiphenyl (52g, 92.8mmol, 1eq) and add 300mL tetrahydrofuran to dissolve,Lower the reaction temperature to -78 C, then dropwise add a 2.5M n-butyllithium / n-hexane solution (142 mL, 185.6 mmol, 2 eq), and stir at constant temperature for 1 h.Dichlorodimethylsilane (35 g, 185.6 mmol, 2 eq) was then added dropwise, stir at constant temperature for 1 h, then return to room temperature and stir for 12 h.After the reaction, it was extracted three times with EA / H2O.The combined organic phases were concentrated to give a crude product.The crude product was purified by silica column chromatography to obtain 17 g of a white solid with a yield of 50%.
45% Step B - Preparation of Compound Int-43cTo a stirred solution of compound Int-43b (2.8 g, 4.9 mmol) in THF (90 mL) at -78 C was added n-BuLi (2.5 M in hexanes, 7.8 mL, 19.5 mmol) dropwise over in -2.5 h. Once the addition was complete, the mixture was allowed to stir for one hour at -78 C whereupon Me2SiCl2 (0.65 mL, 5.4 mmol) was added rapidly. The mixture was allowed to stir for an additional 35 minutes at -78 C, the cooling bath was removed, and the mixture was stirred overnight at rt. Water (10 mL) was added followed by dilution with hexanes (100 mL) and the layers were separated. The organic layer was washed with brine (1 x 25 mL), dried (Na2S04), filtered, and concentrated in vacuo. The crude product was purified using flash chromatography eluting with hexanes to provide 0.82 g (45%) of compound Int- 43c as a white solid
30.1% n-BuLi (2.5 M, 17 mL) was slowly added to the solution of 4,4?-dibromo-2,2?-diiodo-biphenyl (6 g, 10.64 mmol) and THF(100 mL) at 90 C. The solution was kept for 1 h. Afterdichlorodimethylsilane(5.70 g, 44.16 mL) was slowly added to thesolution at the 90 C, the temperature was slowly increased toroom temperature, and stirred for 12 h. The reaction wasterminated by water, and organic layer was extracted by ether.The crude product was purified by n-hexane, and recrystallizedin methanol. Yield: 1.12 g (30.1%) 1H NMR (300 MHz, CD2Cl2):delta 7.68 (d, 2H), 7.63 (d, 2H), 7,5 (s, 2H), 0.43 (s, 6H) 13C NMR(500 MHz, CDCl3): delta 145.7, 141.6, 135.7, 133.4, 122.7, 122.6, 3.25.
under the protection of nitrogen, 5.64 g of 4,4?-dibromo-2,2?-diiodo biphenyl was dissolved in 40 mL of THF, cooled to -25 C., to the solution was added dropwise 20.00 mL of n-butyl lithium solution (n-butyl lithium/n-hexane in 1.0 mol/L). After 2 hours of reaction, 1.29 g of dimethyl dichlorosilane was added, and the reaction was continued for another 24 hours. After the completion of the reaction, a deionized water was added and the resulting mixture was extracted with diethyl ether, then dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product. MALDI-TOF-MS (m/z): 368.1 (M+);
under the protection of nitrogen, 5.64 g of 4, 4'-dibromo-2, 2'-diiodo biphenyl was dissolved in 40 mL of THF, cooled to -25 C, to the solution was added dropwise 20.00 mL of n-butyl lithium solution (n-butyl lithium/n-hexane in 1.0 mol / L). After 2 hours of reaction, 1.29 g of dimethyl dichlorosilane was added, and the reaction was continued for another 24 hours. After the completion of the reaction, a deionized water was added and the resulting mixture was extracted with diethyl ether, then dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product. MALDI-TOF-MS (m / z): 368.1 (M+);

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  • [ 852138-89-7 ]
  • [ 1350306-48-7 ]
  • [ 1350306-46-5 ]
YieldReaction ConditionsOperation in experiment
6.00 g of 4,4?-dibromo-2,2?-diiodobiphenyl was dissolved in 100 mL of a mixed solvent of dichloromethane and ethyl acetate in the volume ratio of 1:1, then cooled to -75 C., and 30.00 mL of phenyl lithium solution (phenyl lithium/n-hexane in 1.0 M,) was added dropwise. Following 10 hours of reaction, 14.56 g of bis-eicosyl dichlorosilane was added, and the reaction was continued for another 34 hours, after the reaction was completed, a water was added and the mixture was extracted with diethyl ether, dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product, MALDI-TOF-MS (m/z): 901.2 (M+);
6.00 g of 4, 4'-dibromo-2, 2'-diiodobiphenyl was dissolved in 100 mL of a mixed solvent of dichloromethane and ethyl acetate in the volume ratio of 1:1, then cooled to -75 C, and 30.00 mL of phenyl lithium solution (phenyl lithium/ n-hexane in 1.0 M,) was added dropwise. Following 10 hours of reaction, 14.56 g of bis-eicosyl dichlorosilane was added, and the reaction was continued for another 34 hours, after the reaction was completed, a water was added and the mixture was extracted with diethyl ether, dried over anhydrous magnesium sulfate, rotary evaporated, and column chromatographed to give the product, MALDI-TOF-MS (m / z): 901.2 (M+),
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