Synthesis
GENERAL METHOD: 3 g (13.8 mmol) of o-bromophenylacetic acid was dissolved in 10 mL of ethanol and the solution was cooled to 0°C. The solution was then cooled to 0°C and the solution was then dried. Under stirring, 1.6 mL (22 mmol) of thionyl chloride was slowly added dropwise. After the dropwise addition was completed, the reaction mixture was gradually heated to 50 °C and kept at this temperature for the reaction overnight. Upon completion of the reaction, the mixture was cooled to room temperature and the solvent was subsequently evaporated under reduced pressure. The residue was mixed with ethyl acetate and filtered through a 6 g column of basic alumina. Finally, the filtrate was evaporated under reduced pressure to give 3.5 g (89% yield) of ethyl (2-bromophenyl) acetate (1d).
References
[1] European Journal of Inorganic Chemistry, 2015, vol. 2015, # 10, p. 1752 - 1758
[2] Patent: WO2009/121919, 2009, A1. Location in patent: Page/Page column 163
[3] Synthesis (Germany), 2015, vol. 47, # 13, p. 1913 - 1921
[4] Organic Letters, 2005, vol. 7, # 22, p. 4963 - 4966
[5] Patent: WO2004/63150, 2004, A2. Location in patent: Page 28
