2,5-Dibromopyridine → 5-Methoxy-3-pyridinecarboxaldehyde

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Reaction Steps

5-Bromo-3-methoxypyridine. To a stirred solution of 2,5-dibromopyridine (2.188 g, 9.2 mmol) in anhydrous MeOH (10 mL) was added NaOMe (10 mL of 25% NaOMe in MeOH, 42 mmol). The mixture was refluxed for 3 days and then poured into a stirred cold aqueous 5% NaHCO3 (75 mL). The mixture was extracted with ether (4×10 mL) and the extracts were washed with brine (3×10 mL). The organic layer was dried (Na2SO4, anhydrous) and evaporated. The crude was purified by chromatography on silica gel with hexane: EtOAc (4:1˜2:1) as eluant, yielding 1.02 g of (61%) the title compound. 1H NMR (CD3OD): 8.17 (s, 1H), 8.12 (s, 1H), 7.24 (s, 1H), 3.74 (s, 3H).

Provenance & Evidence