Sodium Carbonate → 4-(4-Bromophenyl)pyridine

Participants

Reaction Steps

Aq. 2 M sodium carbonate (3 mL)was added to a suspension of 400 mg (2.0 mmol) of 4-bromopyridine in 2 mL of benzene to give 2 clear phases, and argon was bubbled through the mixture for a few minutes before added 115 mg (0.10 mmol) of palladium tetrakis(triphenylphosphine). To the resulting mixture was added a solution of 200 mg (1.00 mmol) of 4-bromophenylboronic acid in 1 mL of ethanol, and the mixture was heated at reflux for 4 h. After cooling to room temperature, the mixture was partitioned between ethyl acetate (25 mL) and water (25 mL). The organic layer was dried over sodium sulfate and concentrated. Purification of the residue by silica gel chromatography, eluting with 25% to 50% ethyl acetate in hexane, gave 193 mg (82%) of 4-(4-bromophenyl)pyridine as a white solid: mp 124-126° C.

Provenance & Evidence