Hexane → 2-Acetyl-6-bromopyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,6-dibromopyridine (0.75 mol) in 2000 ml of anhydrous ether, which was cooled to -60° C. under N2, was added a solution of n-butyllithium in hexane (0.75 mol) over 15 min. The reaction mixture was cooled to -80° C. and a solution of dimethylacetamide (0.86 mol) in 70 ml anhydrous ether was added slowly over 1 hour. After stirring the mixture for 15 min, a solution of NH4Cl (0.93 mol) in 150 ml of water was added slowly over 8 min. After stirring an additional 45 min at room temperature, the aqueous layer was separated and extracted with 500 ml of ether. The combined organic layer was washed with water (2×800 ml), dried (MgSO4), filtered, and stripped on a rotary evaporator to yield 159 g of the desired product. This material was distilled at 80° C./0.1 mm Hg to give a near colorless oil that crystallized readily on cooling.

Provenance & Evidence