Synthesis
General procedure for the synthesis of 3-bromo-2-methylphenol from 3-bromo-2-methylaniline: a solution of sodium was slowly added to a solution of 3-bromo-2-methylaniline (6 g, 32.2 mmol) in sulfuric acid (38.7 mL, 38.7 mmol) at 0 °C. The reaction mixture was stirred at 0°C for 15 minutes before sulfuric acid (13.75 mL, 258 mmol) was added, followed by warming the reaction system to 100°C and heating for 1 hour. After completion of the reaction, the mixture was diluted with water and extracted with ether (Et2O). The organic phase was dried and concentrated and purified by silica gel column chromatography to afford the target product 3-bromo-2-methylphenol (light brown solid, 4.92 g, 82% yield).
References
[1] Chemical Communications, 2003, # 10, p. 1170 - 1171
[2] Patent: US2011/82165, 2011, A1. Location in patent: Page/Page column 46
[3] Journal of Medicinal Chemistry, 2017, vol. 60, # 4, p. 1417 - 1431
[4] European Journal of Organic Chemistry, 2018, vol. 2018, # 17, p. 2013 - 2021
[5] Patent: US6831106, 2004, B1. Location in patent: Page column 19
