Benzoyl Peroxide → Ethyl 2-(bromomethyl)benzoylformate

Participants

Reaction Steps

To a solution of ethyl 2-methylbenzoylformate (10 g) in chlorobenzene (50 ml) were added a solution of bromine (10 g) in chlorobenzene (20 ml) and a suspension of 25%-hydrous benzoyl peroxide (1 g) in chlorobenzene (10 ml) over 2 hours and the mixture was heated under reflux for 1 hour. The reaction mixture was cooled with ice-water and filtered through a pad of celite. The filtrate was concentrated under reduced pressure to give a yellow oil. The oil was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give the desired ethyl 2-(bromomethyl)benzoylformate (1.4 g, yield: 10%).

Provenance & Evidence