Synthesis
A. Triphenylphosphine (0.4 g × 4, 6.1 mmol) was added to a stirred solution of (6-methylpyridin-2-yl)methanol (640 mg, 5.2 mmol) and carbon tetrabromide (2.77 g, 8.35 mmol) in batch to a solution of dichloromethane (12 mL) at 0 °C, each time at 2 min intervals. The reaction was continued for 30 min. Upon completion of the reaction, the reaction mixture was purified using rapid column chromatography using a hexane solution of 10% ethyl acetate as eluent to afford 2-(bromomethyl)-6-methylpyridine as a crystalline solid (675 mg, 70% yield).
References
[1] Journal of the American Chemical Society, 1994, vol. 116, # 18, p. 8410 - 8411
[2] Patent: WO2008/110793, 2008, A1. Location in patent: Page/Page column 112
[3] Patent: WO2008/125839, 2008, A2. Location in patent: Page/Page column 44
[4] Tetrahedron Letters, 2001, vol. 42, # 32, p. 5393 - 5395
[5] Canadian Journal of Chemistry, 2002, vol. 80, # 8, p. 973 - 982
