Toluene → 2-{4-[10-(Biphenyl-4-yl)-9-anthryl]phenyl}benzoxazole

Participants

Reaction Steps

In a 100 mL three-neck flask, 0.91 g (2.0 mmol) of 2-[4-(10-bromo-9-anthryl)phenyl]benzoxazole, 0.44 g (2.2 mmol) of 4-biphenylboronic acid, 0.47 g (4.4 mmol) of sodium carbonate, 10 mL of toluene, 3 mL of ethanol, and 3 mL of water were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 29 mg (0.025 mmol) of tetrakis(triphenylphosphine)palladium(0) was added, and the mixture was stirred under nitrogen stream at 80° C. for 13 hours. After a certain period, the mixture was cooled to room temperature, and the precipitated solid was obtained by suction filtration and washed with water. A toluene solution of the obtained solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene/hexane, giving 0.52 g of the target white powder. Further, an aqueous layer of the filtrate which was obtained through suction filtration after stirring was extracted with toluene. The obtained extracted solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was gravity filtered, and the filtrate was condensed to give a solid. A toluene solution of the solid was subjected to suction filtration through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855) and alumina, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene/hexane, giving 0.47 g of the target white powder. In this manner, a total of 0.99 g of the target white solid was obtained in a yield of 93%.

Provenance & Evidence