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With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 85℃; for 24h;Inert atmosphere;
(2) Under a nitrogen atmosphere,Add the previous step in a 250 ml three-neck round bottom reaction bottle.N,N-biphenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline,420 mg of 4-bromo-3,5-dimethylbenzonitrile, 120 ml of toluene,40 ml of absolute ethanol and 40 ml of a 2 molar solution of potassium carbonate per liter were stirred and dissolved.After 15 minutes of aeration, 50 mg of tetrakis(triphenylphosphine)palladium(0) catalyst was added, and after aeration for 30 minutes, it was heated to 85 C and refluxed for 24 hours. After the reaction was stopped and the reaction was stopped, the solvent of the reaction system was removed by steaming.The reaction system was extracted with a dichloromethane solvent and washed three times with deionized water.It was washed three times with saturated brine and dried over anhydrous magnesium sulfate for 1 hour. The product was purified by column chromatography, and the eluent was a mixture of petroleum ether and dichloromethane in a ratio of 3:1. The yield of the solid product was finally obtained to be 84%.
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 85℃;Inert atmosphere;
(2) Under a nitrogen atmosphere,Add in a 250 ml three-neck round bottom reaction bottle4-bromo-3,5-dimethylbenzonitrile (2 mmol, 420.14 mg) and9,9'-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene) bis ( 9H-carbazole) 1.18g, 2.2mmol),Add 120 mL of toluene and 50 mL of ethanol and stir to dissolve.Further, 40 mL of a saturated potassium carbonate solution (2 mol/L) was added.Quickly join after 15 minutes of ventilationPd(PPh3)4 (173.4 mg, 0.15 mmol) was stirred under nitrogen for 15 min.The reaction system was heated to 85 degrees Celsius overnight.The reaction was stopped, and after the temperature was lowered to room temperature, the solvent of the reaction system was removed by rotary evaporation.Extract with dichloromethane solvent and wash 3 times with deionized water.The product was purified by column chromatography, and the eluent was a mixture solvent of petroleum ether and dichloromethane in a ratio of 3:1.Finally, 597.7 mg of a white solid product was obtained in a yield of 55.3%.The yield of the solid product was finally obtained to be 83%.
3',4',5'-trifluoro-2,6-dimethyl-[1,1'-biphenyl]-4-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
89.2%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; toluene; at 85℃;Inert atmosphere;
Under a nitrogen atmosphere, Add 2.52 g (12 mmol) to a 250 ml three-neck round bottom reaction flask4-bromo-3,5-dimethylbenzonitrile and 2.814 g (16 mmol) of 4,4,5,5-tetramethyl-2-(3,4,5-trifluorophenyl)-1,3, 2-dioxaborolan,Then, 120 ml of toluene, 50 ml of ethanol was added, and then 40 ml of a saturated solution of potassium carbonate (2 mol/L) was added and stirred. After 15 minutes of aeration, tetrakis(triphenylphosphine)palladium 100 mg (0.087 mmol) was added and aeration was continued for 15 minutes. The reaction system was heated to 85 C and stirred at reflux overnight.After the reaction was stopped to return to room temperature, the solvent of the reaction system was removed by rotary evaporation. The reaction system was extracted with dichloromethane and washed three times with deionized water and three times with brine.The product was purified by column chromatography using a mixture of petroleum ether and dichloromethane in a ratio of 3:1.Finally, 2.8 g of a white solid 3',4',5'-trifluoro-2,6-dimethyl-[1,1'-biphenyl]-4-carbonitrile (intermediate product) was obtained.The yield was 89.2%.
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