The general procedure for the synthesis of 1-(bromomethyl)-2-fluoro-3-nitrobenzene from 2-fluoro-3-nitrotoluene was as follows: to a solution of carbon tetrachloride (400 mL) of 2-fluoro-1-methyl-3-nitrobenzene (15.80 g, 101.94 mmol) and N-bromosuccinimide (18.14 g, 101.94 mmol) was added, with stirring, a solution of benzoyl peroxide (0.37 g, 1.52 mmol). The reaction mixture was heated to reflux temperature and kept overnight and subsequently cooled to room temperature. The reaction mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The residue was dissolved in dichloromethane (100 mL) and filtered again. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by medium pressure liquid chromatography (MPLC) on silica gel using a mixture of ethyl acetate and hexane as eluent to give 1-(bromomethyl)-2-fluoro-3-nitrobenzene (8.11 g, 34%) as an off-white solid.1H NMR (400 MHz, CDCl3): δ 8.02 (m, 1H), 7.71 (m. 1H), 7.30 (td, 1H, J=8.4,1.6Hz), 4.55 (d, 2H, J=1.6Hz).
