Sodium borohydride → (5-Bromopyridin-2-yl)methanol

A mixture of 5-bromo-pyridine-2-carbaldehyde (0.5 g, 2.68 mmol) in ethanol (30 mL) was cooled in an ice bath. Sodium borohydride (0.41 g, 10.75 mmol) was added and the reaction mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated, dried, the residue dissolved in dichloromethane (30 mL) and quenched with a saturated aqueous sodium bicarbonate solution. The organic phase was separated and the aqueous phase was extracted further with dichloromethane (2×10 mL). The combined organic phase was dried over sodium sulfate and concentrated to give the product as an off-white solid (426 mg, 84%). 1H NMR (300 MHz, CDCl3): δ (ppm) 8.61 (d, 1H), 7.82 (dd, 1H), 7.23 (d, 1H), 4.73 (s, 2H), 3.92 (bs, 1H).

1. temperaturewas cooled in an ice bath
2. concentrationThe reaction mixture was concentrated
3. customdried
4. dissolutionthe residue dissolved in dichloromethane (30 mL)
5. customquenched with a saturated aqueous sodium bicarbonate solution
6. customThe organic phase was separated
7. extractionthe aqueous phase was extracted further with dichloromethane (2×10 mL)
8. dry with materialThe combined organic phase was dried over sodium sulfate
9. concentrationconcentrated

ORD record

ord-f322264bc9e1404d9f9963eb44343001

Source dataset

uspto-grants-2010_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07790717B2