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CAS No. : | 131222-99-6 | MDL No. : | MFCD00092281 |
Formula : | C18H10Br2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RULVBMDEPWAFIN-UHFFFAOYSA-N |
M.W : | 386.08 | Pubchem ID : | 3286225 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With tri-tert-butyl phosphine; sodium t-butanolate;palladium diacetate; In toluene; at 100℃; | Under argon flow, 6,12-dibromochrysene (3.8 g, 10 mmol), <strong>[626-13-1]m,m'-ditolylamine</strong> (4.9 g, 25 mmol), palladium acetate (0.03 g, 1.5 mol %), tri-t-butylphosphine (0.06 g, 3 mol %), t-butoxysodium (2.4 g, 25 mmol), and anhydrous toluene (100 mL) were added to a 300-mL three-neck flask equipped with a condenser, and the mixture was heated overnight at 100 C. with stirring. After completion of reaction, precipitated crystals were collected through filtration, followed by washing with toluene (50 mL) and methanol (100 mL), to thereby yield 5.5 g of a pale yellow powder. The powder was identified as compound (6) through an NMR spectrum (see FIG. 4) and an FD-MS (yield: 89%). The NMR spectrum was obtained under the same conditions as employed in Synthesis Example 1. |
50% | With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In toluene; at 110℃; for 10.0h;Inert atmosphere; | Di-o-tolyl-amine 1.33 g (6.77 mmol), 6,12-dibromochrysene 1.0 g(2.60 mmol), Pd(OAc)2 0.07 g (0.312 mmol), sodium tert-butoxide 1.5 g(15.6 mmol), and tri-tert-butylphosphine 0.37 mL (0.313 mmol) wereadded to 100 mL of anhydrous toluene in a 3-neck round bottom flaskunder a N2 atmosphere. The mixture was refluxed at 110 C for 10 h.After the reaction was finished, the mixture was extracted withchloroform and DI water. The organic layer was dried with anhydrous MgSO4 and filtered. The solvent was evaporated. The crude productwas purified by column chromatography on silica gel using toluene:hexane=1: 3. (0.8 g, Yield 50%) 1H NMR (300 MHz, THF): delta(ppm)8.63-8.60 (m, 2H), 8.14-8.11 (d, 1H), 7.58-7.52 (t, 1H), 7.47-7.42 (t,1H), 7.09-7.04 (t, 2H), 6.97 (s, 2H), 6.92-6.89 (d, 2H), 6.76-6.73 (d,2H), 2.18 (s, 6H). 13C-NMR (75 MHz, CDCl3): delta=148.88, 143.07,139.43, 132.27, 131.15, 129.35, 128.21, 127.35, 127.19, 125.53,124.08, 122.99, 119.61, 21.80; LRMS(EI, m/z): [M+] calc'd forC46H38N2, 618.30; found, 618; Elemental analysis calc'd (%) forC46H38N2: C 89.28, H 6.19, N 4.53; found: C 88.41, H 6.27, N 4.21%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
23% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In toluene; for 3h;Inert atmosphere; Reflux; | 9,12-dibromochrysene (4.0 g, 10.4 mmol), Compound 4 (4.08 g, 11.5 mmol) according to Synthesis Example 1, and Pd(PPh3)4 (0.48 g, 0.42 mmol) were dissolved in 500 mE of an anhydrous toluene solvent under a nitrogen atmosphere. 50 mE of a 2M K2C03 solution was added thereto. The obtained mixture was heated for 3 hours, while being refluxed under a nitrogen atmosphere. When a reaction was complete, the resultant was extracted with chloroform and distilled water and treated with anhydrous magnesium sulfate. The obtained resulting material was purified by using chloroform: hexane (a volume ratio of 1:7) as an eluting solvent through a silica gel colunm to obtain 1.28 g of a white solid (a yield of 23.0%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95.4% | With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; for 1.5h;Inert atmosphere; Reflux; | In a 1000ml three bottles, with mechanical mixing,Ar gas protection,And 13.5 g (molecular weight: 384, 0.035 mol) of 6,12-dibromo Chrysene,4- (1-naphthyl) benzene boronic acid 8.7 g (molecular weight 248, 0.035 mol)Catalyst Pd (PPh3) 4 dosage1.8 g (molecular weight 1154, 0.001556 mol),Aqueous sodium carbonate solution 120 ml (2M)Toluene 250ml, ethanol 150ml.Stirring reflux, monitoring reaction with TLC,After reaction for 1.5 hs, the reaction was complete.Cooling, separating, drying, separating the product by column chromatography, eluting with 1: 5 ethyl acetate: petroleum ether,To give 17.5 g of a pale yellow solid 6- (4- (1-naphthyl) phenyl) -12-bromo Chrysene having a molecular weight of 508,Purity 97.2%, yield: 95.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; for 20h;Inert atmosphere; Reflux; | 31.4 g (100 mmol) of [4- (2-phenyl-1H-benzimidazol-1-yl) phenyl] boronic acid and 46.1 g (120 mmol) of 6,12-dibromotrile were added to a freshly dried 3000 mL In a double-mouthed bottle,Under nitrogen protection, 20.7 g (150 mmol) of anhydrous potassium carbonate, 2.31 g (2 mmol) of tetratriphenylphosphine palladium, 75 mL of water and 1200 mL of 1,4-dioxane were added.It was then heated under reflux for 20 h.After the reaction was completed, the temperature was lowered to room temperature, and the reaction system was poured into stirred 2 L ice water. At this time, a large amount of light yellow precipitates were generated. Vacuum filtration was performed under reduced pressure, and the filter cake was repeatedly washed with distilled water. Column chromatography was performed with dichloromethane as eluent to obtain a pale yellow mixed solid. Off-white gradient sublimation gave an off-white solid, 25.8 g, yield 45%. |