Hydrochloric Acid → (2-Bromopyridin-3-yl)methanol

Temperature

0 °C

To a mixture of 2-bromonicotinaldehyde (50 g, 0.27 mol), methanol (250 mL) and THF (250 mL) in a 3-necked round bottom flask at 0° C. was added sodium borohydride (10.3 g, 0.27 mol) portion wise. The reaction mixture was stirred at 0° C. for 1 hr and warmed up to room temperature. The reaction mixture was adjusted to pH 7 with 2N HCl (120 mL), and concentrated to remove methanol and THF. The resulting mixture was partitioned between EtOAc and brine three times. The organic layer was combined and washed with brine, dried over Na2SO4, and concentrated to give (2-bromopyridin-3-yl)methanol (51 g), which was used without further purification. LRMS (M+H+) m/z 187.9.

1. temperaturewarmed up to room temperature
2. concentrationconcentrated
3. customto remove methanol and THF
4. customThe resulting mixture was partitioned between EtOAc and brine three times
5. washwashed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated

ORD record

ord-202f1cd59e0041479408410010128ca6

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932270B2