Synthesis
Thionyl chloride (5.80 mL, 80 mmol) was slowly added to methanol (100 mL) under ice bath cooling conditions. After stirring the reaction mixture for 1 hour, a solution of 4-(2-bromoethyl)benzoic acid (4.58 g, 20 mmol) in methanol (30 mL) was added dropwise. The reaction was continued to be stirred at room temperature for 2 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure. Water was added to the residue and extracted with ethyl acetate. The organic layer was washed sequentially with 5% sodium carbonate solution and 5% brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the target product methyl 4-(2-bromoethyl)benzoate (4.79 g, 18.3 mmol, 99% yield) as a colorless oil.
References
[1] Patent: WO2005/12232, 2005, A2. Location in patent: Page/Page column 28-29
[2] Patent: EP1550662, 2005, A1. Location in patent: Page/Page column 27
[3] Patent: WO2005/30135, 2005, A2. Location in patent: Page/Page column 89
[4] Journal of the American Chemical Society, 2010, vol. 132, # 31, p. 10842 - 10846
[5] Patent: WO2011/11186, 2011, A2. Location in patent: Page/Page column 60
