Synthesis
Sodium hydride (60% dispersed in mineral oil, 114 mg, 2.85 mmol) was slowly added to a mixed solution of methanol (0.115 mL, 2.85 mmol) and tetrahydrofuran (0.5 mL) at 0 °C. The reaction mixture was stirred at 0 °C for 15 min before 3,4,5-tribromopyridine (600 mg, 1.900 mmol) was added. Subsequently, the reaction mixture was warmed to room temperature and stirred continuously for 19 hours. Upon completion of the reaction, the reaction mixture was diluted with water (3 mL) and extracted with ethyl acetate (2 x 10 mL). The organic phases were combined, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3,5-dibromo-4-methoxypyridine (0.480 g, 1.798 mmol, 95% yield) as a beige solid. Mass spectrum (electrospray ionization): m/z = 267.9 [M + H]+. 1H NMR (400 MHz, methanol-d4) δ 8.68 (2H, s), 3.99 (3H, s).
