Acetaldehyde → 1-(3,5-Dibromopyridin-4-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

To a cooled (−78° C.) solution of 3,5-dibromo-pyridine (2.0 g, 8.4 mmol) in dry THF (80 mL) is added LDA in THF solution (2M; 5.1 mL, 10.1 mmol) and the mixture is stirred at −78° C. for 2 h. Acetaldehyde in THF solution (5M; 3.4 mL, 16.9 mmol) is added and the mixture is stirred at −78° C. for 30 min, then at room temperature for 16 h. Saturated aqueous NH4Cl solution is added and the mixture is extracted with EtOAc. The organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 2.9 g (67% purity) of 1-(3,5-dibromo-pyridin-4-yl)-ethanol.

Provenance & Evidence