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[ CAS No. 114772-54-2 ] {[proInfo.proName]}

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Chemical Structure| 114772-54-2
Chemical Structure| 114772-54-2
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Quality Control of [ 114772-54-2 ]

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Product Details of [ 114772-54-2 ]

CAS No. :114772-54-2 MDL No. :MFCD00671503
Formula : C14H10BrN Boiling Point : -
Linear Structure Formula :- InChI Key :LFFIEVAMVPCZNA-UHFFFAOYSA-N
M.W : 272.14 Pubchem ID :1501912
Synonyms :
Chemical Name :4'-(Bromomethyl)-[1,1'-biphenyl]-2-carbonitrile

Calculated chemistry of [ 114772-54-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.07
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 69.43
TPSA : 23.79 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.7
Log Po/w (XLOGP3) : 3.83
Log Po/w (WLOGP) : 3.97
Log Po/w (MLOGP) : 3.64
Log Po/w (SILICOS-IT) : 4.53
Consensus Log Po/w : 3.73

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.36
Solubility : 0.0118 mg/ml ; 0.0000433 mol/l
Class : Moderately soluble
Log S (Ali) : -4.03
Solubility : 0.0257 mg/ml ; 0.0000944 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.26
Solubility : 0.000151 mg/ml ; 0.000000553 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.43

Safety of [ 114772-54-2 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P270-P271-P264-P280-P362+P364-P303+P361+P353-P301+P330+P331-P301+P312+P330-P304+P340+P310-P305+P351+P338+P310-P405 UN#:3261
Hazard Statements:H302+H312+H332-H314 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 114772-54-2 ]

* 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 [ 114772-54-2 ]

[ 114772-54-2 ] Synthesis Path-Downstream   1~10

  • 1
  • [ 57113-90-3 ]
  • [ 114772-54-2 ]
  • [ 139481-38-2 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In acetonitrile; at 80 - 85℃; for 5h;Heating / reflux; Industry scale; methyl 2-t-butoxycarbonylamino-3-nitrobenzoate [BAN] obtained in Reference Example 3 (354 kg), a solution of 4-(2-bromomethylphenyl)benzonitrile [BMB] in acetonitrile obtained in Reference Example 4 (1), and anhydrous potassium carbonate (475 kg) were added to acetonitrile (1600 kg), and the mixture was heated (80 to 85 C) under reflux for about 5 hours.. The reaction solution was cooled, and the insoluble were separated and washed with acetonitrile (320 kg).. The filtrated washing was concentrated under reduced pressure to give concentrate of methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].
  • 2
  • [ 114772-53-1 ]
  • [ 209911-63-7 ]
  • [ 114772-54-2 ]
YieldReaction ConditionsOperation in experiment
82 - 84% With N-Bromosuccinimide; Azo-bis(2,4-dimethyl-valeronitril); In dichloromethane; at 45 - 50℃; for 2 - 5h;Industry scale; 23 g of 2-(4-methylphenyl)benzonitrile [MPB], 22g of N-bromosuccinic acid imide [NBS] and 47 mg of 2,2'-azobis(2,4-dimethylvaleronitrile) were suspended in 44 ml of dichoromethane, and the reaction was allowed to proceed at 45 to 50C for 5 hours under stirring. 46 ml of water was added, and the layers were separated to obtain organic layer (The same procedure was carried out three times totally).. The organic layer was concentrated, and 50 ml of acetonitrile was added.. The solution was concentrated again, and 50 ml of acetonitrile was added thereto to obtain 116 g of a solution of 2-(4-bromomethylphenyl)benzonitrile [BMB] in acetonitrile (yield calculated from a quantitated value of 2-(4-bromomethylphenyl)benzonitrile: 84 %). 30.1 g of methyl 2-tert-butoxycarbonylamino-3-nitrobenzoate [BAN], 40.8 g of potassium carbonate and 160 ml of acetonitrile were added to the acetonitrile solution in which unreacted 2-(4-methylphenyl)benzonitrile [MPB] and 2-(4,4-dibromomethylphenyl)benzonitrile as an analogue of BMB were contaminated, and the reaction was allowed to proceed at about 82 C for about 5 hours under stirring.. After cooling to room temperature, the precipitated crystals were filtered off, and the filtrate was concentrated to give methyl 2-[N-t-butoxycarbonyl-N-[(2'-cyanobiphenyl-4-yl)methyl]amino]-3-nitrobenzoate [BBN].. The concentrated material was dissolved in 190 g of methanol, and 106 g of concentrated hydrochloric acid was added dropwise thereto.. The resulting solution was heated to a reflux temperature over 2 hours, and stirred for 2 hours under reflux, whereby, the reaction was allowed to proceed.. The reaction solution was cooled, and precipitated crystals were collected by filteration and dried to give 35.1 g of methyl 2-[N-(2'-cyanobiphenyl-4-yl)methylamino]-3-nitrobenzoate [MBN] (yield relative to 2-(4-methylphenyl)benzonitrile [MPB] was 76.1 %). Reference Example 4 (1)Synthesis of 4-(2-bromomethylphenyl)benzonitrile [BMB] 2-(4-Methylphenyl)benzonitrile [MPB] (271 kg), N-bromosuccinic acid imide [NBS] (256 kg), 2,2'-azobis(2,4-dimethylvaleronitrile) [ABN-V] (543 kg) and methylene chloride (680 kg) were stirred at 45 to 50 C under reflux, and the reaction was allowed to proceed until an area percentage of 4-(2-boromomethylphenyl)benzonitrile [BMB] with HPLC became 82 % or more (about 2 to 5 hours).. After the reaction solution was cooled to 38 to 42 C, methylene chloride (250 kg) was added.. Water (540 L) was added, the layers were separated, the resulting aqueous layer was extracted with 50 kg of methylene chloride, and the organic layers were combined (this procedure was repeated three times totally).. The methylene chloride layer was concentrated to about 700 L (about 2.5-fold volume of MPB) under atmospheric pressure (inner temperature: about 46 C).. acetonitrile (about 640 kg) was added thereto, the resulting solution was concentrated to about 1100 L under reduced pressure (about 200 to 450 MmHg) while maintaining the inner temperature at 45 to 55 C (desirably 45 to 50 C).. Then, acetonitrile (about 480 kg) was added, and the resulting solution was concentrated to about 500 L under reduced pressure (about 200 to 450 MmHg) while maintaining the inner temperature at 45 to 55 C (desirably 45 to 50 C).. acetonitrile (about 480 kg) was added to the residue, whereby the amount of solution came to about 1100 L, to give a solution containing 2-(4-bromomethylphenyl)benzonitrile [BMB], unreacted 2-(4-methylphenyl)benzonitrile [MPB] and 2-(4,4-dibromomethylphenyl)benzonitrile as an analogue of BMB in acetonitrile.
10 - 20%; 80 - 90% With sodium bromate; hydrogen bromide; In dichloromethane; water; at 0 - 20℃;UV-irradiation; A jacketed 1,000 mL 3-neck flask was charged with 4'-methylbiphenyl-2-carbonitrile (Compound 1, 100.0 g) and CH2Cl2 (500 mL) under nitrogen. To a 500 mL Erlenmeyer flask with magnetic stirrer, sodium bromate (NaBrO3; 31.2 g) was dissolved in water (170 mL). The NaBrO3 solution was transferred to the 1,000 mL flask and the reaction mixture was cooled to about 5 C. or less. Aqueous HBr solution (48%, 105.0 g) was added to the 1,000 mL flask and the resulting reaction mixture was recycled though a UV lamp reactor. The reaction mixture was kept at 0-20 C. and the recycling was continued until the reaction was deemed complete by HPLC. Optionally, additional sodium bromate and hydrogen bromide may be added. The relative amounts of Compound 2 and Compound 3 were about 80-90% and about 10-20% respectively. Aqueous sodium metabisulfite solution (2.0 g of in 10 mL water) was added to the reaction mixture. Allow the phases to settle and the methylene chloride phase was washed with water and used in the next step without further purification.
69% With sodium bromate; azobis(2-cyanobutane); bromine; In water; chlorobenzene; at 70 - 80℃; for 6h; Production Example; Chlorobenzene (652.5 g) was added with 4'-methyl-2-cyanobiphenyl (416.2 g, 2.251 mole) and sodium bromate (57.41 g, 0.38 mole) dissolved in water (109 g), and the mixture was warmed at 75 to 80C. A solution of 2,2'-azobis(2-methylbutyronitrile) (8.31 g, 0.043 mole) dissolved in monochlorobenzene (87 g) was dropped together with bromine (217.5 g, 1.116 mole) into the mixed solution above at 70 to 80C over 5 hours, then leaving it for 1 hour with maintaining its temperature. The solution was set still at about 80C and then subjected to phase separation. The organic layer was added with 217.5 g of water, washed at about 80C and then subjected to phase separation. The separated solution was concentrated under a reduced pressure to eliminate 91.4 g of chlorobenzene. The residual solution was added with 304.5 g of chlorobenzene to filter at 75 to 80C by a filter pre-coated with 11 g of diatomaceous earth. Washing with 208.8 g of chlorobenzene, then the filtrate was cooled down after confirming no precipitation of crystal observed therein. The filtrate was added with 450 mg of seed crystal at the temperature thereof of about 50C, and stirred at 55C for 6 hours. Then, this solution was cooled down in the rate of 10C/hour, followed by stirring at the temperature thereof of 30 to 35C for 5 hours and at the temperature thereof of 0 to -5C for 10 hours, and then being subjected to filtration. By rinsing the crystal with heptane, 404.6 g of 4'-bromomethyl-2-cyanobiphenyl was obtained in the yield of 69 %.
With sodium bromate; azobis(2-cyanobutane); bromine; In water; chlorobenzene; at 70 - 85℃; for 5h; Example 2: Production of CBAL (1) To monochlorobenzene (450 g) was added CMB (300 g, 1.55 mol), and solution prepared by dissolving sodium bromate (50.1 g, 0.33 mol) in 95.3 g of water was added. 2,2'-azobis(2-methylbutyronitrile)(2.0 g, 0.01 mol) was dissolved in monochlorobenzene(10g), and this solution was added to the above-mentioned solution at 75 to 85C, then, immediately, solution prepared by dissolving 2,2'-azobis(2-methylbutyronitrile)(89 g, 0.05 mol) in monochlorobenzene (48.8 g), and bromine (198.5 g, 1.24 mol) were dropped simultaneously respectively at 70 to 80C. The solution of 2,2'-azobis(2-methylbutyronitrile) was dropped at a rate of about 0.22 g/min and bromine was dropped at a rate of about 0.73 g/min. The added solution was stirred for 5 hours at 70 to 75C, and the reaction solution was checked under HPLC analysis conditions (1), and that the area percentage of raw materials reached 1% or less was confirmed, obtaining a mixed solution of CMBMB and CDBMB. The solution was analyzed under the HPLC analysis conditions (1), to find an area percentage of CMBMB of 63.6%, CDBMB of 36.2% and a raw material CMB of 0.2%.
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In dichloromethane; at 40 - 45℃; for 4 - 5h; Example- 1Bromination of 4-methyl-2'-cyanobiphenyl (OTBN)100 g OTBN was added to 500 ml dichloromethane, 100 g NBS and 5 g AIBN were added to the reaction mixture. The mixture was then stirred at 400C to 45C for 4 to 5 hours and then monitored by HPLC. After cooling to room temperature, the organic layer was washed with water (2 x 100 ml). Dichloromethane was stripped off. The residue was dried under vacuum to get 140 g of cake (Composition by HPLC (Unquantified area%)- Br-OTBN- 84%+ dibromo-OTBN - 11% + OTBN - 5%)

  • 3
  • [ 209911-63-7 ]
  • [ 114772-54-2 ]
  • [ 135689-93-9 ]
YieldReaction ConditionsOperation in experiment
78% With hexamethylenetetramine; acetic acid; In water; chlorobenzene; at 85 - 90℃; for 12h;Product distribution / selectivity; (2) To monochlorobenzene (720 g) was added water (420 g), acetic acid (662 g) and hexamethylenetetramine (653 g, 4.66 mol), then, the whole amount of the brominated reaction solution of CMB obtained above was added, and the above-mentioned reaction vessel was washed with monochlorobenzene (120 g), and the washing solution was added to the reaction solution. The resulting solution was stirred at about 90C for 11 hours. The stirred solution was allowed to stand still at 85 to 90C for 1 hour, and aqueous layer was separated and removed. To organic layer was added water (840 ml), pH was adjusted to 7.8 with 10% potassium carbonate aqueous solution (540g), and the solution was allowed to stand still. Aqueous layer was separated and removed, then, 150 ml of monochlorobenzene was distilled off under a reduced pressure of 40 to 50 kPa at 85 to 90C. The resulting solution was cooled to 75C, seed crystals were added, then, the mixture was stirred at the same temperature for 2 hours. The mixture was cooled at a rate of 10C/hour, and aged at 8 to 12C for 6 hours. Filtration was performed, and the resulting crystals were washed with monochlorobenzene (420 g) cooled to about 5C, and dried at about 60C to obtain CBAL (250.9 g). The yield was 78%.
  • 4
  • [ 209911-63-7 ]
  • [ 114772-54-2 ]
  • 2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one hydrochloride [ No CAS ]
  • [ 138401-24-8 ]
YieldReaction ConditionsOperation in experiment
85 - 88% With potassium hydroxide; phosphonic acid diethyl ester;methyl tributylammonium chloride; In dichloromethane; water; at -5 - 30℃; A 1 L 3-neck flask was charged with Compound V (134.0 g), MTBAC (5.0 g) and CH2Cl2 (170 mL) and cool to -5 to 5 C. An aqueous solution of KOH (182.6 g in 212 mL water) was added slowly to the 1 L flask and the reaction temperature was kept at 5 C. The methylene chloride solution of Compound IVa and Compound IVb from Example 1 was added to the reaction mixture slowly, while maintaining the temperature at 0-10 C. Diethyl phosphite (39.66 g) was added drop wise at 0-10 C. Check the reaction mixture for completion of the reduction reaction, and additional diethyl phosphite may be added. The reaction mixture was allowed to warm to ambient (20-30 C.) and agitated until the reaction was deemed complete by HPLC. Water (150 mL) was added and the phases were separated. The organic layer was extracted with water (230 mL) and polish filtered. The methylene chloride (which contained the crude Compound II) was distilled off and exchanged with about 400 mL of methyl tert-butyl ether (MTBE) (optionally, the MTBE recycled from washing below can be used here). Upon cooling, crystallization occurred (optionally seeds were added) and after further cooling to below 25 C., crystals of Compound II were isolated, washed with MTBE and dried in vacuum at a temperature of less than 60 C. HPLC retention time: 18.126 min. Typically, the yield was about 85 to about 88%. Alternatively, IPA could be used as the crystallization and washing solvent. Optionally, the solvent (i.e., MTBE or IPA) used to wash the crystals of Compound II above can be recycled and used to crystallize the crude Compound II in the next batch. Since the washed solvent contains Compound II as well as impurities, it was surprisingly found that the washed solvent can be recovered and used again in crystallizing the crude compound of formula II in the next batch without sacrificing its purity while increasing its yield.
  • 5
  • [ 209911-63-7 ]
  • [ 114772-54-2 ]
  • [ 114772-53-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogen;platinum on carbon; In n-heptane; water; at 60 - 70℃; under 7.35576 - 29.423 Torr; Example; In a 500ml four-neck flask, 300g of filtrate before heptane rinsing of the above described Production Example (according to determination by HPLC-ES method; 4'-bromomethyl-2-cyanobiphenyl 4.75 %, <strong>[209911-63-7]4'-dibromomethyl-2-cyanobiphenyl</strong> 3.93 % and 4'-methyl-2-cyanobiphenyl 5.43 %: according to determination by HPCL area percentage method; 4'-bromomethyl-2-cyanobiphenyl 28.4 %, <strong>[209911-63-7]4'-dibromomethyl-2-cyanobiphenyl</strong> 23.5 % and 4'-methyl-2-cyanobiphenyl 32.5 %), 85 g of water, 2.52 g of activated carbon and 2.52 g of 5 % Pt/C (50 % wet) were added, followed by replacing the atmosphere thereof with nitrogen, and then the mixture was subjected to hydrogenation reaction at 60 to 70C under 100 to 400 mmH2O pressure of hydrogen. The HPCL area percentage values after completion of the reaction were 0.31 % of 4'-bromomethyl-2-cyanobiphenyl, non-detected <strong>[209911-63-7]4'-dibromomethyl-2-cyanobiphenyl</strong> and 82.7 % of 4'-methyl-2-cyanobiphenyl. Solid, mainly the catalyst and activated carbon, was separated by filtration, followed by separation of water layer from the filtrate to obtain an organic layer. The organic layer was washed with aqueous caustic soda solution and then with salt solution, followed by phase separation. Chlorobenzene in the organic phase was evaporated under a reduced pressure, followed by subjecting the residual solution to reduced-pressure distillation to obtain 32 g of 4'-methyl-2-cyanobiphenyl. Its dehalogenation yield was 95 % and purity was 98 %.
  • 6
  • [ 150058-27-8 ]
  • [ 114772-54-2 ]
  • [ 139481-44-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In methanol; at 50 - 55℃; for 24h; To 80.0 grams (0.363 moles) of methyl 2-ethoxybenzimidazole-7-carboxylate were added 400 ml of methanol, 99 grams of potassium carbonateand 94 grams of 4-bromomethyl-2'-cyanobiphenyl, and the resulting mixture wasstirred at ambient temperature for 24 hours. The reaction mass was quenchedwith chilled 2400 ml of water, filtered and washed with 160ml of water. The wetsolid was washed with 370 ml of hot ethyl acetate, and then dried at 50-60°C toget 105.0 grams of methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-7-carboxylate, substantially free from methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-benzimidazole-4-carboxylate.;150 g of 2-ethoxy-3H-benzoimidazole-4-carboxylic acid methyl ester, 750 ml.of methanol, 231.8 g of 4'-Bromomethyl-biphenyl-2-carbonitrile and 235.2 g ofpotassium carbonate were charged in a four neck round bottom flask equippedwith a half moon shaped Teflon type blade. The reaction mixture was heated toabout 50-55°C and was maintained under stirring for about 3-4 hours. Cooled thereaction mixture to about 25-35°C. Charged 6 liters of water in a four neck roundflask followed by cooling to about 0-5°C.The reaction mass was added to thewater under stirring over about 10-30 minutes under stirring and was stirredfurther for about 1-2 hours. Separated solid was filtered and washed with 300 ml.of water. The wet compound was charged in a four neck round bottom flask followed by charging 2250 ml of ethyl acetate. Reaction suspension was heated toabout 70-75°C and was stirred for about 30-45 minutes. Reaction suspension wascooled to about 0-5°C and was stirred for about 1-2 hours. Separated solid wasfiltered and washed with 150 ml of ethyl acetate. Solid obtained was dried at about60-65°C for about 3-5 hours to yield 177 g of title compound of Formula (V);
With potassium carbonate; In acetone;Reflux; To a 500 mL flask was added 200 mL of acetone,Ethoxybenzimidazole-7-carboxylate (XIII, 22.0 g,0.10 mol),K2CO3 (17.9 g, 0.13 mol) and 4-bromomethyl-2'-cyanobiphenyl (28.6 g, 0.105 mol).The temperature was raised to reflux and reaction was complete until TLC disappeared (about 5 to 8 hours).
  • 7
  • [ 21230-43-3 ]
  • [ 114772-54-2 ]
  • ethyl 3-[N-(2'-cyanobiphenyl-4-yl)methylamino]-1-methylpyrazole-4-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With potassium carbonate; In ice-water; N,N-dimethyl-formamide; a) Ethyl 3-[N-(2'-cyanobiphenyl-4-yl)methylamino]-1-methylpyrazole-4-carboxylate To a mixture of <strong>[21230-43-3]ethyl 3-amino-1-methylpyrazole-4-carboxylate</strong> (P. Schmidt et al. Hel. Chim. Acta., 1959, 41, 349.) (2.30 g) and potassium carbonate in N,N-dimethylformamide (70 ml), was added portionwise 4-bromomethyl-2'-cyanobiphenyl (4.81 g). The solvent was distilled under reduced pressure. To the residue was added ice-water and an aqueous solution of potassium carbonate. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give crude crystals, which were recrystallization from ethyl acetate-isopropylether to afford the title compound as white crystals (3.7 g, 76%), m.p. 151-152 C. 1 H-NMR(200 MHz, CDCl3) delta: 1.32(3H,t), 3.74(3H,s), 4.25(2H,q), 4.58(2H,d), 5.73(1H,bd), 7.33-7.70(8H,m), 7.75 (1H,d). IR(nujol)cm-1: 3390, 2220, 1685, 1565, 1555, 1365, 1245, 1160, 1120.
  • 8
  • [ 57113-90-3 ]
  • [ 114772-54-2 ]
  • [ 139481-28-0 ]
YieldReaction ConditionsOperation in experiment
2-Tert-butoxy carbonylamino-3-nitro benzoic acid methyl ester (400 gm) was dissolved in toluene (2000 ml) and then added potassium carbonate (400 gm) at room temperature. 4-(2-cyanophenyl)benzyl bromide (400 gm) and Tetra-n-butylammonium bromide were added to the reaction mass. Gradually temperature raised to 80 to 85C. The reaction mass maintained for 12 hours at 80 to 85C. The reaction mass was cooled to room temperature and filtered on hiflo-bed. Collected the filtrate and concentrated to remove toluene. To the residue was added methanol (800 ml) and cooled to room temperature. The reaction mass was stirred for 4 hours at room temperature and filtered. Methanol (2900 ml) was added to the wet compound obtained and then added concentrated hydrochloric acid (725 ml) at room temperature. The reaction mass was heated to reflux and maintained for 3 hours at reflux. The reaction mass was further cooled to room temperature and filtered. Methanol (2900 ml) was added to the wet compound obtained and stirred for 45 minutes at room temperature. The separated solid was filtered and dried at 45 to 50C for 6 hours to obtain 450 gm of 2-(2'-cyanobiphenyl- 4-yl-methylamino)-3-nitro benzoic acid methyl ester.
  • 9
  • [ 21543-49-7 ]
  • [ 114772-54-2 ]
  • 4'-[(6-chloropyridin-3-yl)methoxy]methyl}biphenyl-2-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% (6-Chloropyridin-3-yl)methanol (4.3 g) was dissolved in tetrahydrofuran (150 mL), and the solution was cooled to 0 C. Sodium hydride (63%, 1.4 g) was added thereto, and the mixture was stirred at 0 C. for 1 hour. Subsequently, 4′-(bromomethyl)biphenyl-2-carbonitrile (9.0 g) was added thereto at 0 C., and the mixture was stirred at 50 C. for 19 hours. The reaction solution was brought back to room temperature, and a saturated aqueous ammonium chloride solution was added thereto. After extraction with ethyl acetate, the organic layer was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (Moritex Corporation, elution solvent: hexane/ethyl acetate) to obtain the title compound (6.2 g) as a white solid (yield: 62%). [0332] 1H-NMR (400 MHz, CDC3) δ: 8.39 (1H, d, J=2 Hz), 7.78 (1H, d, J=8 Hz), 7.72 (1H, dd, J=8 Hz, 2 Hz), 7.66 (1H, dt, J=8 Hz, 2 Hz), 7.57 (2H, d, J=8 Hz), 7.52 (1H, d, J=8 Hz), 7.48 (2H, d, J=8 Hz), 7.45 (1H, dt, J=8 Hz, 2 Hz), 7.35 (1H, d, J=8 Hz), 4.66 (2H, s), 4.60 (2H, s).
  • 10
  • [ 114772-54-2 ]
  • [ 147403-52-9 ]
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Nitriles

Chemical Structure| 22115-41-9

[ 22115-41-9 ]

2-Cyanobenzyl bromide

Similarity: 0.91

Chemical Structure| 28188-41-2

[ 28188-41-2 ]

3-(Bromomethyl)benzonitrile

Similarity: 0.91

Chemical Structure| 17201-43-3

[ 17201-43-3 ]

4-Cyanobenzyl bromide

Similarity: 0.91

Chemical Structure| 72054-56-9

[ 72054-56-9 ]

4-(2-Bromoethyl)benzonitrile

Similarity: 0.85

Chemical Structure| 209911-63-7

[ 209911-63-7 ]

4'-(Dibromomethyl)-[1,1'-biphenyl]-2-carbonitrile

Similarity: 0.85

; ;