3,5-Dimethoxyphenol → HCID 21964056, compound

Under an argon atmosphere, a solution of 3,5-dimethoxyphenol (6.94 g, 45 mmol) in dimethylformamide (30 mL) was added slowly to a stirred suspension of sodium hydride (1.44 g of a 75% suspension in mineral oil, 0.045 mol) in dimethylformamide (30 mL) at 0–5° C. The icebath was removed and the resulting mixture was stirred for 2.5 h at room temperature. 3,5-Dibromopyridine (7.11 g, 0.03 mol) was added to the mixture, which was then heated to 100° C. for 72 h, then the mixture was cooled to room temperature and successively washed with water (100 mL) and 5 N NaOH solution (10 mL). The mixture was extracted with diethyl ether (3×50 mL). The combined organic phases were dried (MgSO4), filtered and concentrated by rotary evaporation to give 9.2 g of a white solid, which was purified by column chromatography, eluting with cyclohexane/ethyl acetate (90/10, v/v). Selected fractions containing the product were concentrated via rotary evaporation to give 2.5 g (29%) of a yellow oil.

1. customThe icebath was removed
2. temperaturewas then heated to 100° C. for 72 h
3. temperaturethe mixture was cooled to room temperature
4. washsuccessively washed with water (100 mL) and 5 N NaOH solution (10 mL)
5. extractionThe mixture was extracted with diethyl ether (3×50 mL)
6. dry with materialThe combined organic phases were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated by rotary evaporation

ORD record

ord-19e9fb7ec28845bf9fd4be6d942bd712

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07101896B2