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)-diazen-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, the insoluble material was filtered off, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (ethyl acetate/hexane=0/100→5/95) to give the title compound (3.42 g, 66%) as a colorless oil.

Provenance & Evidence