General procedure for the synthesis of 2-fluoro-6-bromobenzenemethanol from 2-bromo-6-fluorobenzaldehyde: Sodium borohydride (284 g, 7.93 mol) was added batchwise to a solution of 2-bromo-6-fluorobenzaldehyde (1.60 kg, 7.91 mol) in methanol (14 L) at 0 °C, with a controlled rate of addition to regulate exothermic and gas production. After 15 minutes of reaction, the reaction was quenched with water (500 mL) and the reaction mixture was subsequently concentrated to give a yellow oil. The oil was dissolved in ethyl acetate (6L) and washed with (3L) water. The aqueous layer was back-extracted with ethyl acetate (1L). The organic phases were combined, washed with brine (2L), dried over anhydrous sodium sulfate, filtered and concentrated to give 2-fluoro-6-bromobenzenemethanol as an orange oil (1614 g, 100%). The product was characterized by 1H NMR (CDCl3): δ 7.40 (d, 1H), 7.18 (m, 1H), 7.07 (t, 1H), 4.86 (s, 2H).
