N-bromobutanimide → 5-Bromo-2-(bromomethyl)pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-bromo-2-methylpyridine (5.0 g) in carbon tetrachloride (50 mL) was added N-bromosuccinimide (6.2 g) and 2,2′-azobis(2-methylpropionitrile) (239 mg) and the mixture was stirred at 85° C. for 1 hour. After cooling, the reaction mixture was filtered to remove the insoluble materials and the filtrate was concentrated in vacuo. The resultant crude product was purified by a column chromatography on silica gel (solvent; hexane/ethyl acetate=100:0→92:8) to give 5-bromo-2-bromomethyl-pyridine (3.7 g, yield: 51%).

Provenance & Evidence