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

Participants

Reaction Steps

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.

Provenance & Evidence