N-bromobutanimide → Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-chloro-3-methylbenzoate (3.60 g, 19.4 mmol) in acetonitrile (60 mL) were added 1-bromopyrrolidine-2,5-dione (11.46 g, 64.3 mmol) and 2,2′-(E)-diazene-1,2-diylbis(2-methylpropanenitrile) (960 mg, 5.84 mmol), and the mixture was stirred at 90° C. for 26 hr. The reaction mixture was concentrated, insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/0→95/5) to give the title compound (3.42 g, 66%) as a colorless oil.

Provenance & Evidence