Synthesis
General procedure for the synthesis of 2-bromo-5-fluorobenzyl alcohol from 2-bromo-5-fluorobenzaldehyde: To a solution of 2-bromo-5-fluorobenzaldehyde (75.0 g, 369 mmol) in ethanol (375 mL) was slowly added a solution of sodium borohydride (4.47 g, 118 mmol) in water (9 mL) at 0 °C. The reaction mixture was kept stirred at 0°C for 1 hour. Upon completion of the reaction, the mixture was treated with water and ethyl acetate and extracted with ethyl acetate. The combined organic extracts were washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure to give 75.6 g of 2-bromo-5-fluorobenzyl alcohol (yield = 99.8%) as a colorless solid.1H NMR (CDCl3) δ 7.50-7.46 (1H, m), 7.29-7.25 (1H, m), 6.92-6.85 (1H, m), 4.72 (2H, s).
References
[1] Journal of Organic Chemistry, 2005, vol. 70, # 2, p. 756 - 759
[2] Patent: WO2007/19098, 2007, A2. Location in patent: Page/Page column 44
[3] Tetrahedron, 2007, vol. 63, # 38, p. 9401 - 9405
[4] Patent: CN108358961, 2018, A. Location in patent: Paragraph 0016; 0057; 0058-0060; 0062; 0069; 0071; 0078
[5] CrystEngComm, 2014, vol. 16, # 23, p. 4999 - 5011
