Dimethylformamide → 1-(4-Methylphenyl)pyrene

Participants

Reaction Conditions

Reaction Steps

A mixed solution of 45 g of 1-bromopyrene, 21.7 g of 4-methylphenylboronic acid, 34 g of tribasic potassium phosphate, 10.3 g of tetrabutylammonium bromide, 0.71 g of palladium acetate, and 1.6 l (liters) of dimethylformamide was heated and stirred at 120° C. for 5 hours under a nitrogen stream. After the mixture was cooled to room temperature, 1.6 l of water was added thereto and stirred at room temperature for 0.5 hours. The precipitated solid was separated by filtration and washed twice with 200 ml of water. The resulting solid was dissolved in 500 ml of dichloromethane. The solution was dried over magnesium sulfate and then filtered through celite. The filtrate was evaporated, and the resulting residue was washed twice with 200 ml of methanol. The precipitated solid was separated by filtration and dried under vacuum to give 40 g of 1-(4-methylphenyl)pyrene.

Provenance & Evidence