1-(3-BroMo-4-fluorophenyl)ethanol

Synthesis

General procedure for the synthesis of 1-(3-bromo-4-fluorophenyl)ethanol from 1-(3-bromo-4-fluorophenyl)ethan-1-one: sodium borohydride (2.1 g, 55.5 mmol) was added batchwise to a mixture of 1-(3-bromo-4-fluorophenyl)ethan-1-one (10 g, 46 mmol) in a solution of tetrahydrofuran (THF, 100 mL) and methanol (1.0 mL) . The reaction mixture was heated to 70 °C and maintained for 1 h, followed by cooling to room temperature. Upon completion of the reaction, the reaction was quenched with 1N hydrochloric acid solution (100 mL) and extracted with ethyl acetate (EtOAc, 3 x 100 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate (MgSO4) and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to afford 1-(3-bromo-4-fluorophenyl)ethanol (9.8 g, 97% yield).1H NMR (400 MHz, CDCl3) δppm: 1.48 (d, J=6.15 Hz, 3H), 7.24-7.33 (m, 1H), 7.59 (dd, J=6.59,2.20 Hz, 1H).

References

[1] Patent: WO2006/76246, 2006, A2. Location in patent: Page/Page column 155
[2] Patent: US2007/3539, 2007, A1. Location in patent: Page/Page column 80
[3] Tetrahedron Letters, 2007, vol. 48, # 31, p. 5471 - 5474
[4] European Journal of Organic Chemistry, 2011, # 23, p. 4409 - 4414
[5] Patent: WO2018/81047, 2018, A1. Location in patent: Page/Page column 185