Sodium hydride → 5-bromo-2-(2,2-difluoroethoxy)pyridine

2,2-Difluoroethanol (0.40 ml) was added dropwise to a suspension of sodium hydride (0.270 g) in dimethylformamide (5 ml) cooled in an ice-bath under argon. The mixture was stirred at room temperature for 40 minutes, then re-cooled in an ice-bath. A solution of 2,5-dibromopyridine (1 g) in dimethylformamide (5 ml) was added. The solution was then heated at 65° C. under argon for 18 h, allowed to cool and diluted with water (50 ml). The aqueous phase was extracted three times with ethyl acetate. The combined extracts were washed with water, brine, dried over magnesium sulphate, filtered and evaporated. The product was purified by column chromatography eluting with hexane to give a colourless oil (0.946 g).

1. temperaturecooled in an ice-bath under argon
2. temperaturere-cooled in an ice-bath
3. temperatureThe solution was then heated at 65° C. under argon for 18 h
4. temperatureto cool
5. extractionThe aqueous phase was extracted three times with ethyl acetate
6. washThe combined extracts were washed with water, brine
7. dry with materialdried over magnesium sulphate
8. filtrationfiltered
9. customevaporated
10. customThe product was purified by column chromatography
11. washeluting with hexane

ORD record

ord-038ab2017e4d432cb07e30f1f08f219f

Source dataset

uspto-grants-2011_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07956084B2