Sodium Carbonate → 1-Bromo-6-phenylpyrene

Participants

Reaction Conditions

Reaction Steps

Next, 18.0 g (50.0 mmol) of 1,6-dibromopyrene, 6.10 g (50.0 mmol) of phenylboronic acid, and 1.16 g (1.0 mmol, 2 mol %) of tetrakis(triphenylphosphine)palladium(0) were loaded into a 300-ml three-necked flask, and air in the container was replaced with argon. Further, 150 ml of toluene and 75 ml (3 eq) of a 2M aqueous solution of sodium carbonate were added to the mixture, and the whole was refluxed under heat in an oil bath at 100° C. for 8 hours. After one night, the precipitate was separated by filtration, and the filtrate (toluene solution) was purified by column chromatography, whereby 11.6 g of 1-phenyl-6-bromopyrene were obtained (64.6% yield).

Provenance & Evidence