Ammonium Chloride → (5-Bromo-3-pyridinyl)methanol

To a stirred solution of 5-bromonicotinaldehyde (5 g, 26.9 mmol) in ethanol (Volume: 100 mL) was added sodium borohydride (0.610 g, 16.13 mmol) slowly over five min at ambient temperature. A half hour later, the reaction mixture was placed in an ice bath then slowly added 50 mL saturated ammonium chloride and stirred for 5 min. After that the reaction mixture was concentrated in vacuo to provide a white solid to which was partitioned between water and ether. The ethereal layer was dried over magnesium sulfate, and concentrated to give a clear liquid of (5-bromopyridin-3-yl)methanol (4.8 g, 24.25 mmol, 90% yield). 1H NMR (500 MHz, DMSO-d6) δ 8.59 (d, J=2.1 Hz, 1H), 8.51 (d, J=1.5 Hz, 1H), 8.01-7.93 (m, 1H), 5.46 (t, J=5.6 Hz, 1H), 4.55 (d, J=5.5 Hz, 2H), Mass spec.: 188.0 (MH)+.

1. customA half hour later, the reaction mixture was placed in an ice bath
2. concentrationAfter that the reaction mixture was concentrated in vacuo
3. customto provide a white solid to which
4. customwas partitioned between water and ether
5. dry with materialThe ethereal layer was dried over magnesium sulfate
6. concentrationconcentrated

ORD record

ord-189e6315c27f405da599aa799944df00

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691821B2