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-ed0c8e490cda477c89b16743c96742bb

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08236805B2