To a methanolic solution of 5-fluoro-2-methoxybenzaldehyde (11.093 g, 1 eq., purchased from Aldrich Chemical Company) was added sodium borohydride (7.515 g, 2.7 eq.) in batches at -10 °C and under nitrogen protection. The reaction solution was slowly warmed to room temperature and stirred for 30 minutes before the methanol solvent was removed by reduced pressure distillation and replaced with dichloromethane. The reaction mixture was poured into ice water and extracted with dichloromethane. The organic phases were combined, dried with magnesium sulfate and concentrated under reduced pressure to remove the solvent to give 5-fluoro-2-methoxybenzyl alcohol as a colorless oil (9.794 g, 87% yield).1H NMR (300 MHz, CDCl3) δ: 2.58 (m, 1H), 3.81 (s, 3H), 4.63 (d, 2H, J=6.3 Hz), 6.78 (dd, 1H J=8.9 and 4.3 Hz), 6.94 (td, 1H, J=8.5 and 3.1 Hz), 7.04 (dd, 1H, J=8.7 and 3.1 Hz).
