To a solution of 3-bromo-4-fluorobenzyl alcohol (5.00 g, 24.4 mmol) in anhydrous N,N-dimethylformamide (50 mL) was added a suspension of 60% sodium hydride in mineral oil (1.37 g, 34.2 mmol) in batches at 0 °C. The reaction mixture was stirred at 0 °C for 30 min. Subsequently, iodomethane (4.15 g, 29.3 mmol) was added at the same temperature. The mixture was gradually warmed to room temperature and stirring was continued for 1 hour. Upon completion of the reaction, the reaction was quenched by the addition of water (200 mL) and extracted with ethyl acetate (3 x 200 mL). The organic layers were combined, washed with brine (50 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuum and the residue was purified by column chromatography using a petroleum ether solution of 2% to 5% ethyl acetate as eluent to afford the target product 2-bromo-1-fluoro-4-methoxymethylbenzene as a colorless oil (4.50 g, 84% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.57 (dd, J=6.4,2.0 Hz, 1H), 7.28-7.23 (m, 1H), 7.11 (t, J=8.0 Hz, 1H), 4.42 (s, 2H), 3.41 (s, 3H).
