Hydrochloric Acid → 2-Acetyl-6-bromopyridine

Participants

Reaction Steps

12.5 mL of a solution of n-BuLi 1.6 M in hexane (20 mmol) are added at −78° C. to a solution of 4.70 g 2,6-dibromopyridine 20 (20 mmol) in 100 mL anhydrous ether. The reaction medium is left in the cold for 30 min. 2 mL N,N-dimethylacetamide are added cold (−78° C.) for 1 h, then allowed to reach the ambient temperature. The reaction medium is neutralized with 25 mL of an aqueous HCl 1M solution. The aqueous phase is extracted with Et2O (3×20 mL). The combined organic phases are washed with brine (3×20 mL), dried on MgSO4, filtered, then evaporated under vacuum. The raw product is recrystallized in an Et2O/n-C5H12 (1/2) mixture. 1.18 g of an orange solid is obtained, i.e. a 28% yield.

Provenance & Evidence