Sulfuryl chloride → 2-Chloro-1-(4-methylpyridin-2-yl)propan-1-one

HRID 1059905

Reaction equation

HRID 1059905 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8](=[O:11])[CH2:9][CH3:10])[CH:3]=1.S(Cl)([Cl:15])(=O)=O>C(Cl)(Cl)Cl>[Cl:15][CH:9]([CH3:10])[C:8]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:7]=[CH:6][N:5]=1)=[O:11]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 186309841-(4-Methylpyridin-2-yl)propan-1-one

Product 1

HCID 186674842-Chloro-1-(4-methylpyridin-2-yl)propan-1-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 1-(4-methylpyridin-2-yl)propan-1-one (0.9 g) in chloroform (5 ml) was added a solution of sulfuryl chloride (0.533 ml) in chloroform (5 ml) dropwise. The resultant mixture was refluxed for 2 hours and evaporated under reduced pressure. The pH was adjusted to 8.5 with a saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate twice. The combined organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (silica gel 25 g, n-hexane:dichloromethane=1:1) to give 2-chloro-1-(4-methylpyridin-2-yl)propan-1-one (0.71 g).

Workup

  1. customevaporated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate twice
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography (silica gel 25 g, n-hexane:dichloromethane=1:1)

Sources & evidence

ORD record
ord-85ffa0499c814ce1bfe6c4a830ea5708
Source dataset
uspto-grants-2003_02
Patent number
US06521643B1

Linked notes

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