Benzoyl Peroxide → 3-(bromomethyl)-1-methylpyridin-2(1H)-one

Participants

Reaction Steps

N-Bromosuccinimide (2.17 g, 12.2 mmol) and benzoic peroxyanhydride (0.295 g, 1.22 mmol) were added to a flask containing a solution of 1,3-dimethylpyridin-2(1H)-one (1.50 g, 12.2 mmol) in carbon tetrachloride (250 mL, degassed with flowing N2 for 5 minutes). The mixture was heated at reflux for 3 hours. The reaction mixture was cooled to ambient temperature, filtered through filter paper, and the filtrate was concentrated under vacuum. The residue was suspended in diethyl ether (20 mL), stirred for 15 minutes, and the liquid was decanted. The solids were rinsed with diethyl ether (3×5 mL), then dried under vacuum to give 3-(bromomethyl)-1-methylpyridin-2(1H)-one as a yellow solid (1.1 g).

Provenance & Evidence