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

HRID 274060Notes

Reaction equation

HRID 274060 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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24648Sulfuryl chlorideHCID 115791671-(6-Chloropyridin-2-yl)ethanone

Product 1

HCID 155504512-Chloro-1-(6-chloropyridin-2-YL)ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

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.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel with a mixture of n-hexane and toluene (1:1) as an eluent

Sources & evidence

ORD record
ord-2b5d1454342e4719acf4d5a437d30dd9
Source dataset
uspto-grants-1995_02
Patent number
US05387710

Reaction notes

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