2-Bromo-4-pyridinecarboxaldehyde → 1-(2-Bromopyridin-4-yl)ethanol

To a chilled (−78° C.) solution of 2-bromo-pyridine-4-carbaldehyde (10.0 g, 53.8 mmol) in THF (100 mL) was added a 3 M solution of methylmagnesium chloride in THF (18 mL, 54 mmol) over a 10 minute period. After 1 hour, the yellow solution was allowed to warm gradually to room temperature over a 3 hour period. The reaction was quenched by the slow addition of saturated aqueous NH4Cl (50 mL) and extracted with EtOAc (2×200 mL). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated to afford a brown oil. The crude material was purified by silica gel chromatography eluting with a gradient of 10-45% EtOAc in hexanes to afford 1-(2-bromo-pyridin-4-yl)-ethanol.

1. customThe reaction was quenched by the slow addition of saturated aqueous NH4Cl (50 mL)
2. extractionextracted with EtOAc (2×200 mL)
3. washThe combined organic layers were washed with brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customto afford a brown oil
7. customThe crude material was purified by silica gel chromatography
8. washeluting with a gradient of 10-45% EtOAc in hexanes

ORD record

ord-c02cda5a25c04c6984a2a0b9aee0fedb

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08163918B2