N-bromobutanimide → 2-(Bromomethyl)-4-fluoro-1-nitrobenzene

Participants

Reaction Steps

574 g (3.70 mol) of 5-fluoro-2-nitrotoluene and 659 g (3.70 mol) of N-bromosuccinimide were introduced into 3.7 l of chloroform, 30.0 g (183 mmol) of 2,2′-azobis-2-methylpropanenitrile were added, and the mixture was heated under reflux with irradiation by a UV lamp for 18 h. Cooling was followed by filtration with suction, and the filtrate was concentrated, the residue was taken up in diethyl ether and filtered with suction, and the filtrate was concentrated. The residue was dissolved in dichloromethane and petroleum ether and purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate gradient) to result in 92.0 g (10% of theory) of the title compound.

Provenance & Evidence