5-Bromopyridine-2-carboxylic acid → (5-Bromopyridin-2-yl)methanol

To a solution of 5-bromopyridin-2-carboxylic acid (8 g, 42.1 mmol) in THF (100 ml) was added borane-dimethylsulphide (16 ml, 168.30 mmol) dropwise at 0° C. After warming-up to ambient temperature stirring was continued for 24 hours. The solution was cooled again to 0° C., quenched with MeOH and refluxed for 1 h. Solvents were removed and the residue was treated with water. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with water and brine, dried, filtered and concentrated under reduced pressure to afford 4.76 g (64%) of the title compound.

1. temperatureThe solution was cooled again to 0° C.
2. customquenched with MeOH
3. temperaturerefluxed for 1 h
4. customSolvents were removed
5. additionthe residue was treated with water
6. extractionThe aqueous phase was extracted with ethyl acetate
7. washthe combined organic layers were washed with water and brine
8. customdried
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-e740b3385ae6473ca736d7a7acca7af1

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08703768B2