(6-Methoxypyridin-3-yl)methanol (250 mg, 1.797 mmol, commercially available from e.g. Fluorochem) was used as starting material, which was dissolved in chloroform (20 mL) in a 50 mL round bottom flask. Phosphorus tribromide (0.188 mL, 1.989 mmol) was slowly added dropwise to the reaction system at 0 °C. After the reaction was completed, the reaction was stopped and the reaction was completed. After the dropwise addition, the reaction mixture was stirred at room temperature for 1 hour. After completion of the reaction, the reaction mixture was washed with water (3 x 30 mL) and the organic layer was separated. The organic phases were combined, washed with saturated saline (30 mL), filtered through a hydrophobic glass stock and concentrated under reduced pressure to remove the solvent. The resulting oily crude product was dissolved in dichloromethane and purified by column chromatography on a Biage Isolera SNAP 25g silica gel with an elution gradient of 0-4% cyclohexane/ethyl acetate. The fraction containing the target product was collected and concentrated under reduced pressure to give 5-(bromomethyl)-2-methoxypyridine (160 mg, 0.792 mmol, 44% yield) as a colorless oil.The results of LCMS (2 mM formic acid) analysis were: retention time (Rt) = 0.93 min, [M+H]+ = 202.
