Hydrogen Bromide → 1-Phenyl-2-(4-pyridinyl)ethanone

Participants

Reaction Conditions

Reaction Steps

A solution of diisopropylamine (22 mL, 15.03 mmol) in THF (200 mL) under argon atmosphere was cooled to −78° C. BuLi (96 mL of a 1.6 M solution in hexane, 153.0 mmol) was added dropwise. After 1 h, a solution of 4-methylpyridine (15.00 g, 161.1 mmol) in THF (75 mL) was added and allowed to warm to 0° C. At this temperature it was stirred for 30 minutes. It was cooled to −78° C. and benzonitrile (18.27 g, 177.2 mmol) in THF (75 mL) was added and stirred at −78° C. for 2 h. It was stirred at room temperature overnight. Water (225 mL) was added, it was cooled with a water-ice bath and adjusted to pH 1 with 48% HBr. The organic phase was separated. The aqueous phase was heated to reflux for 2 h, allowed to cool and extracted with diethyl ether. The aqueous phase was taken to neutral pH with 1 N NaOH and extracted with EtOAc. The organic phase was dried over Na2SO4 and concentrated to dryness, to afford 28.53 g of title compound (yield: 90%).

Provenance & Evidence