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

Temperature

0 °C

The 5-bromo-pyridine-2-carbaldehyde (2.0 g) was taken up in MeOH and cooled to 0° C. Sodium borohydride (450 mg) was added in portions at 0° C. The solution was warmed to 25° C. and stirred at that temperature for 1.5 h. The solution was concentrated, and the residue was quenched with 1 M HCl(aq.). The solution was stirred at 25° C. for 0.5 h. The solution was rendered basic via addition of solid K2CO3. The mixture was extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered, and concentrated to give (5-bromo-pyridin-2-yl)-methanol as a white solid.

1. temperatureThe solution was warmed to 25° C.
2. concentrationThe solution was concentrated
3. customthe residue was quenched with 1 M HCl(aq.)
4. stirringThe solution was stirred at 25° C. for 0.5 h
5. additionThe solution was rendered basic via addition of solid K2CO3
6. extractionThe mixture was extracted with CH2Cl2
7. dry with materialThe combined organic layers were dried (MgSO4)
8. filtrationfiltered
9. concentrationconcentrated

ORD record

ord-8c0eefc32a6f4683815a241cef35359e

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07700597B2