Hydrochloric Acid → 6-Bromopyridine-2-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

2,6-Dibromopyridine (25 g, 0.105 mol) is suspended in 200 ml of ether. The solution is cooled to -78° C. and n-butyllithium (65.6 ml, 1.6M, 0.105 mol) in hexane is added slowly dropwise over a 1.5 hour period. After 5 minutes, dimethylformamide (8.4 g, 0.115 mol) in 13 ml of ether is added slowly dropwise over one hour. The reaction is allowed to stir at -78° C. for 1.5 hours. The mixture is warmed to -25° C. and 40 ml of 6N hydrochloric acid is added. The mixture is allowed to warm to room temperature. The aqueous phase is extracted three times with ether and the combined organics are washed once with water, dried over sodium sulfate and evaporated. Trituration with pentane afforded 15.0 g of the title compound as a tannish-white solid.

Provenance & Evidence