Synthesis
General procedure for the synthesis of 1-(2-bromo-5-methoxyphenyl)ethan-1-ol from 1-(2-bromo-5-methoxyphenyl)ethanone: To a solution of 1-(2-bromo-5-methoxyphenyl)ethan-1-ol (3.8 g, 16.5 mmol) in methylene chloride (100 mL) was added pyridinium chlorochromate (PCC, 8.4 g, 33.0 mmol). The reaction mixture was stirred at room temperature for 16 hours. After completion of the reaction, the mixture was filtered and the filtrate was concentrated. The crude product was purified by silica gel fast column chromatography with the eluent of petroleum ether/ethyl acetate (5:1) to afford 1-(2-bromo-5-methoxyphenyl)ethanone (3.6 g, 95% yield) as an off-white solid.1H NMR (300 MHz, CDCl3) δ 7.45 (d, 1H), 6.96 (d, 1H), 6.82 (dd, 1H) 4.38 (q, 2H), 3.80 (s, 3H), 2.62 (s, 3H).
References
[1] Organic Letters, 2012, vol. 14, # 2, p. 628 - 631
[2] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 7, p. 550 - 554
[3] Patent: WO2013/22740, 2013, A2. Location in patent: Paragraph 0393; 0395
[4] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2059 - 2074
[5] Synthetic Communications, 2014, vol. 44, # 14, p. 2076 - 2087
