145908-29-8

Methyl 4-chloro-2-methylbenzoate (10.86 g, 58.8 mmol, 1.0 eq.) was used as the starting material and dissolved in carbon tetrachloride (100 mL). N-bromosuccinimide (15.7 g, 88.2 mmol, 1.5 eq.) and benzoyl peroxide (0.05 g) were added sequentially. The reaction mixture was heated to reflux overnight. After completion of the reaction, the reaction mixture was filtered and the solids were washed with dichloromethane. The organic filtrates were combined, concentrated and dried to afford the target product methyl 2-bromomethyl-4-chlorobenzoate (7.1 g, 45.8% yield). The structure of the product was confirmed by 1H NMR.

[1] Patent: US2005/143348, 2005, A1. Location in patent: Page/Page column 45; 49; 55
[2] Patent: US2005/239838, 2005, A1. Location in patent: Page/Page column 41
[3] Patent: WO2005/54176, 2005, A1. Location in patent: Page/Page column 136
[4] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 5, p. 1628 - 1631
[5] Patent: US2009/270393, 2009, A1. Location in patent: Page/Page column 43-44