2-Bromo-3-methoxypyridine

Chemical Properties

Uses

Synthesis Reference(s)

Synthesis

6602-32-0

74-88-4

24100-18-3

Under nitrogen protection, sodium hydride (605 mg, 15.1 mmol) was added in batches to ice-cooled methanol (10 mL). After stirring for 20 min, a solution of 2-bromo-3-hydroxypyridine (2.5 g, 14.4 mmol) in dimethylformamide (20 mL) was added to the reaction system. Subsequently, methanol was removed by distillation under reduced pressure and iodomethane (0.94 mL, 15.1 mmol) was added to the residue. The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the mixture was concentrated to dryness and the residue was treated with water (50 mL) and ether (50 mL). The organic layer was separated and washed sequentially with saturated aqueous sodium bicarbonate and brine. The organic phase was dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Finally, the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 8:1) to afford the target compound 2-bromo-3-methoxypyridine (1.51 g, 56% yield) as colorless needle-like crystals. The product was confirmed by 1H-NMR (400 MHz, CDCl3): δ 3.90 (3H, s), 7.12 (1H, m), 7.21 (1H, dd, J = 4.8, 8.0 Hz), 7.97 (1H, m). IR (ATR) showed characteristic absorption peaks: 1556, 1410, 1076, 1049, 788 cm-1. The melting point is 34°C.

References