Dimethylformamide → 1-(4-Methylphenyl)pyrene

Participants

Reaction Conditions

Reaction Steps

A mixed solution of 45.0 g of 1-bromopyrene, 21.7 g of 4-methylphenylboronic acid, 34.0 g of tripotassium phosphate, 10.3 g of tetrabutylammonium bromide, 0.71 g of palladium acetate and 1.6 L of dimethylformamide was heated and stirred under a nitrogen gas stream at 120° C. for 5 hours. The solution was cooled to room temperature and 1.6 L of water was poured into the solution, followed by stirring at room temperature for 0.5 hours. The precipitated solid was collected by filtration and then washed twice with 200 ml of water. The resulting solid was dissolved in 500 ml of dichloromethane, dried over magnesium sulfate and then filtered through Celite. The filtrate was evaporated and the residue was washed twice with 200 ml of methanol, and then the precipitated solid was collected by filtration and vacuum-dried to obtain 40.0 g of 1-(4-methylphenyl)pyrene.

Provenance & Evidence