GENERAL STEPS: To a solution of 4-bromo-2-fluoro-1-nitrobenzene (2.0 g, 9.09 mmol) in methanol (50 mL) was added a methanolic solution of 30% sodium methanolate (1.64 g, 9.09 mmol). The reaction mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was concentrated and the residue was dissolved in water (30 mL) and extracted with ethyl acetate (2 x 30 mL). The organic phases were combined, washed with water, separated, dried over anhydrous magnesium sulfate, filtered, and the solvent was evaporated under reduced pressure to give 5-bromo-2-nitroanisole as a crystalline solid (2.1 g, 99% yield).1H-NMR (DMSO-d6): δ [ppm] 7.9 (d, 1H), 7.6 (s, 1H), 7.3 (d, 1H), 4.0 (s, 3H).
