Hydrochloric Acid → 2-Chloro-1-(6-chloropyridin-2-YL)ethanone

Reaction equation

[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[N:5]=1)(=[O:3])[CH3:2].Cl.S(Cl)([Cl:15])(=O)=O>O1CCOCC1>[Cl:10][C:6]1[N:5]=[C:4]([C:1]([CH2:2][Cl:15])=[O:3])[CH:9]=[CH:8][CH:7]=1

Participants

Procedure

A solution of 2-acetyl-6-chloropyridine (7.48 g) in 1,4-dioxane (112 ml) was added 4N hydrogen chloride in 1,4-dioxane (12.6 ml). To the solution, sulfuryl chloride (13.51 ml) was added dropwise at 30° C. After stirring for 0.5 hour, ice water (150 ml) was added to the solution and the organic layer was separated, washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of n-hexane and toluene (1:1) as an eluent to give chloromethyl 6-chloro-2-pyridyl ketone (7.05 g) as a powder.