Ethanol → Bis(biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]amine

Participants

Reaction Conditions

Reaction Steps

2-Bromo-9,9-dimethyl-7,10-diphenylacridan (2.9 g), bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboran-2-yl)phenyl]amine (4.0 g), toluene (44 ml), ethanol (11 ml), and a 2M potassium carbonate aqueous solution (8.4 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (0.23 g) and stirred at 72° C. for 4.5 hours. The mixture was allowed to cool to a room temperature, and an organic layer was collected by a liquid separating operation. The organic layer was dried with magnesium sulfate and concentrated under reduced pressure to obtain a red crude product. The crude product was dissolved by adding toluene (75 ml), purified by adsorption using silica gel (5.2 g), and purified by recrystallization using toluene/methanol to obtain a whitish powder of bis(biphenyl-4-yl)-[4-(9,9-dimethyl-7,10-diphenylacridan-2-yl)phenyl]amine (3.19 g; yield 64%).

Provenance & Evidence