Phosphorus tribromide → 1-(Bromomethyl)-2-methyl-4-nitrobenzene

To a solution of (2-methyl-4-nitrophenyl)methanol (2 g, 12 mmol) in DCM (25 ml) in an ice-water bath under nitrogen was added a solution of phosphorous tribromide (1.13 ml, 12 mmol, Aldrich) in DCM (20 ml). The resulting solution was allowed to warm to ambient temperature and stirred for 2 h. The reaction mixture was poured onto ice-water (70 ml) and saturated sodium hydrogen carbonate (30 ml). The mixture was diluted with DCM (50 ml) and the phases separated. The aqueous extract was washed with DCM (20 ml). The combined organic extracts were washed with water (50 ml), dried (MgSO4), filtered and the solvent removed in vacuo to leave 1-(bromomethyl)-2-methyl-4-nitrobenzene as a yellow solid (1.5 g).