Acetophenone → HCID 86652883, compound

Participants

Reaction Conditions

Reaction Steps

At −78° C. a 2.5 M solution of n-butyl lithium (18.6 mL, 46.4 mmol, 1.1 equiv) was added dropwise to 2,6-dibromopyridine (1) (10.0 g, 42.2 mmol, 1.0 equiv) in THF (780 mL). The solution was then stirred for 20 min at which point acetophenone (5.06 g, 44.3 mmol, 1.0 equiv) was added. The reaction was allowed to stir an additional 0.5 hr at −78° C., at this time the cooling bath was removed and the reaction allowed to warm room temperature. The reaction was stirred at room temperature for 1 hr and quenched with saturated sodium bicarbonate (250 mL). The layers were separated and the aqueous layer extracted with dichloromethane (250 mL). The combined organic layers were dried over sodium sulfate and absorbed onto silica gel (30 g) by concentration under reduced pressure. This material was then purifies on a silica gel column (300 g) by eluting with heptanes (1 L), ethyl acetate (2%) in heptanes (2 L), ethyl acetate (5%) in heptanes (2 L) and finally ethyl acetate (10%) in heptanes (1 L). The desired product was isolated pure in 40% yield (4.7 g).

Provenance & Evidence