N-bromobutanimide → 3-Bromo-2-(bromomethyl)pyridine

Participants

Reaction Steps

3-Bromo-2-methylpyridine (10.0 g, 58.1 mmol), diphenylperoxyanhydride (2.82 g, 11.6 mmol), 1-bromopyrrolidine-2,5-dione (10.9 g, 61.0 mmol) were refluxed in 233 mL of carbon tetrachloride for 144 hours. The reaction mixture was cooled to ambient temperature and washed with water (3×200 mL). The organic layer was dried over Na2SO4, filtered, concentrated, and purified by silica gel chromatography eluting with 0-30% EtOAc in hexanes to provide 3-bromo-2-(bromomethyl)pyridine.

Provenance & Evidence