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Under a nitrogen atmosphere, a solution of 3-bromo-5-hydroxymethylpyridine (379 mg, 2.0 mmol) in dry tetrahydrofuran (10 mL) was treated at ambient temperature with sodium hydride (160 mg, 4.0 mmol, 60% dispersion in mineral oil). After stirring 5 min at ambient temperature, the opaque, yellow mixture was treated with methyl iodide (342 mg, 2.4 mmol). After stirring 2 h at ambient temperature, the mixture was added to cold water (30 mL) and extracted with diethyl ether (3×20 mL). The combined ether extracts were dried (Na2SO4), filtered, and concentrated by rotary evaporation to an orange oil (429 mg). Purification by column chromatography on silica gel, eluting with 15% (v/v) ethyl acetate in hexane afforded 266 mg (65.3%) of 3-bromo-5-methoxymethylpyridine as a colorless oil.

1. stirringAfter stirring 2 h at ambient temperature
2. extractionextracted with diethyl ether (3×20 mL)
3. dry with materialThe combined ether extracts were dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated by rotary evaporation to an orange oil (429 mg)
6. customPurification by column chromatography on silica gel
7. washeluting with 15% (v/v) ethyl acetate in hexane