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

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).

1. temperatureThe mixture was refluxed for 3 days
2. extractionThe mixture was extracted with ether (4×10 mL)
3. washthe extracts were washed with brine (3×10 mL)
4. dry with materialThe organic layer was dried (Na2SO4, anhydrous)
5. customevaporated
6. customThe crude was purified by chromatography on silica gel with hexane: EtOAc (4:1˜2:1) as eluant

ORD record

ord-865c979edd7f4e18ac079e3c16662c45

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053117B2