Hydrochloric Acid → 1-(5-Chloropyridin-2-yl)ethan-1-one

Participants

Reaction Conditions

Reaction Steps

5-Chloropyridine-2-carbonitrile (10.7 g, 77 mmol) was dissolved in diethyl ether (65 mL) and THF (35 mL) under a nitrogen atmosphere. The mixture was cooled until the internal temperature was −63° C. Methylmagnesium bromide (3M in THF, 35 mL, 105 mmol) was added over 30 min. The reaction mixture was then left stirring at −60° C. for 45 min and was then warmed to room temperature. THF (50 mL) was added to dissolve any precipitated material and the reaction mixture was stirred for 1 h. 2M HCl aq. (100 mL) was added and the reaction mixture was stirred for 4 h. The pH was then adjusted to 7 with sodium bicarbonate. The phases were separated and the product extracted from the aqueous phase with DCM. The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. The product was purified by flash column chromatography (eluent heptane:EtoAc gradient) to yield 7.9 g (64% yield) of the title compound.

Provenance & Evidence