N-bromobutanimide → 2-Bromo-5-bromomethylpyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-5-methylpyridine (5 g, 29 mmol) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (7.79 g, 44 mmol). The mixture was heated to 80° C., then dibenzoyl peroxide (53 mg, 0.22 mmol) was added and the mixture was stirred at 80° C. for 4 h then cooled to room temperature, washed with water and brine, dried over Na2SO4, filtered and evaporated. The residue was chromatographed on silica gel (30% EtOAc/heaxanes) to give 6 g of 2-Bromo-5-(bromomethyl)pyridine (MS+H, 251.8).

Provenance & Evidence