Methyl 2-(broMoMethyl)nicotinate

65719-09-7

116986-08-4

General procedure for the synthesis of methyl 2-(bromomethyl)nicotinate from methyl 2-methylnicotinate: methyl 2-methylnicotinate (4.1 g, 27.1 mmol), N-bromosuccinimide (NBS, 5.8 g, 32.5 mmol) and azobisisobutyronitrile (AIBN, 100 mg, 0.61 mmol) were dissolved in carbon tetrachloride (55 mL). The reaction mixture was stirred at 90 °C for 16 h under nitrogen protection. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was diluted with water (25 mL), followed by extraction of the aqueous layer with dichloromethane (50 mL x 3). The organic layers were combined and concentrated under reduced pressure to remove the solvent, and the resulting crude product was purified by silica gel column chromatography to afford the target product methyl 2-(bromomethyl)nicotinate (5.0 g, 80.6% yield). The product was analyzed by LCMS, m/z: 229.9 ([M+H]+).