Synthesis
General procedure for the synthesis of 2-bromo-5-(chloromethyl)pyridine from 2-bromo-5-(hydroxymethyl)pyridine: (6-bromopyridin-3-yl)methanol (1.000 g) was dissolved in dichloromethane (DCM, 10 mL) and cooled to 0°C. Thionyl chloride (1.260 g) was added slowly dropwise with stirring. After the dropwise addition was completed, the ice bath was removed and the reaction mixture was allowed to warm naturally to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction solution was concentrated directly to give 1.050 g of 2-bromo-5-(chloromethyl)pyridine.
References
[1] Patent: WO2006/114213, 2006, A1. Location in patent: Page/Page column 30
[2] Patent: US5420270, 1995, A
[3] Journal of Medicinal Chemistry, 2012, vol. 55, # 7, p. 3201 - 3215
[4] Inorganic Chemistry, 2016, vol. 55, # 16, p. 7944 - 7953
[5] Journal of Biological Inorganic Chemistry, 2018, vol. 23, # 7, p. 1139 - 1151
