Synthesis
Thionyl chloride (3 mL) was added slowly and dropwise to a solution of 3-fluoro-4-methylbenzoic acid (13.23 g, 85.85 mmol) in anhydrous ethanol (200 mL) at 0 °C. The reaction mixture was warmed to 60 °C and stirred overnight. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently concentrated under reduced pressure. The concentrate was diluted with dichloromethane and the resulting organic phase was washed sequentially with 1N sodium hydroxide solution (100 mL x 2). The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give ethyl 3-fluoro-4-methylbenzoate (15.02 g, 96% yield).
References
[1] Patent: WO2011/71565, 2011, A1. Location in patent: Page/Page column 163
[2] Patent: WO2010/93845, 2010, A1. Location in patent: Page/Page column 153
[3] Journal of Medicinal Chemistry, 1983, vol. 26, # 9, p. 1282 - 1293
[4] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 5, p. 1421 - 1425
[5] Patent: WO2009/145360, 2009, A1. Location in patent: Page/Page column 129-130
