3,5-Dibromopyridine → 3-Bromo-5-methoxypyridine

Temperature

150 °C

A mixture of 3,5-dibromopyridine (20.00 g, 84.42 mmol), sodium methoxide (11.40 g, 211.06 mmol), and copper powder (1 g, 5% by weight of 3,5-dibromopyridine) in dry methanol was heated in a sealed glass tube at 150° C. for 14 h. The reaction mixture was cooled to ambient temperature and extracted with diethyl ether (4×200 mL). The combined ether extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over aluminum oxide, eluting with ethyl acetate-hexane (1:9, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing 9.40 g (59.5%) of a colorless oil, which tended to crystallize upon cooling.

1. temperatureThe reaction mixture was cooled to ambient temperature
2. extractionextracted with diethyl ether (4×200 mL)
3. dry with materialThe combined ether extracts were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated by rotary evaporation
6. customThe crude product was purified by column chromatography over aluminum oxide
7. washeluting with ethyl acetate-hexane (1:9, v/v)
8. concentrationconcentrated by rotary evaporation

ORD record

ord-09fd8f9d727142508ea55fc4ba3a17b7

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07045538B2