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

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

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

ORD record

ord-5fb2cbf4d81443f78fd49ed53828441b

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927550B2