N-bromobutanimide → 5-(Bromomethyl)-2-chloro-3-fluoropyridine

Participants

Reaction Steps

In 80 ml of carbon tetrachloride, 4.00 g (27.6 mmol) of 2-chloro-3-fluoro-5-methylpyridine was dissolved. To this solution, 7.37 g (41.4 mmol) of N-bromosuccinimide and 20 mg of benzoyl peroxide were added, and the mixture was heated under reflux overnight. After completion of the reaction, the reaction liquid was returned to room temperature, and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1). Thus, 3.06 g of 5-(bromomethyl)-2-chloro-3-fluoropyridine was obtained (Percentage Yield: 51%).

Provenance & Evidence