Methanol → 2-Bromo-3-methoxypyridine

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Reaction Steps

Under a nitrogen atmosphere, sodium hydride 60% in oil (605 mg, 15.1 mmol) was added in portions to methanol (10 ml) under ice cooling. Twenty minutes later, a dimethylformamide (20 ml) solution of 2-bromo-3-hydroxypyridine (2.5 g, 14.4 mmol) was added. From the resulting mixture, methanol was distilled off under reduced pressure. To the residue was added methyl iodide (0.94 ml, 15.1 mmol), followed by stirring at room temperature for 3 hours. After the reaction mixture was concentrated to dryness, water (50 ml) and ether (50 ml) were added to the concentrate. The organic layer was separated and washed with a saturated aqueous solution of sodium bicarbonate and brine. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to remove the solvent. The residue was purified by silica gel chromatography (hexane:ethyl acetate=8:1) to give the title compound (1.51 g, 56%) as colorless needle crystals.

Provenance & Evidence