Sulfuryl chloride → 1-Chloro-1-(isopropylsulfonyl)propan-2-one

HRID 220354Notes

Reaction equation

HRID 220354 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH:6]([S:9]([CH2:12][C:13](=[O:15])[CH3:14])(=[O:11])=[O:10])([CH3:8])[CH3:7]>CC(O)=O.C(Cl)Cl>[Cl:4][CH:12]([S:9]([CH:6]([CH3:8])[CH3:7])(=[O:11])=[O:10])[C:13](=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 229086371-(Isopropylsulfonyl)propan-2-one

Product 1

HCID 581806351-Chloro-1-(isopropylsulfonyl)propan-2-oneYield 157.9%

Reagents, catalysts & solvents 1

HCID 21922555Acetic acid methylene chlorideSolvent

Procedure

Sulfuryl chloride (0.248 mL, 3.05 mmol) was added dropwise to a solution of 1-(isopropylsulfonyl)propan-2-one (418 mg, 2.55 mmol) in 1:1 AcOH/DCM (16 ml) at 0° C. The reaction was stirred at rt for 4 h. The solvent was removed in vacuo, then diluted with dichloromethane. The organic layer was washed (2×) with saturated NaHCO3 solution, dried over Na2SO4, filtered, and concentrated to leave 800 mg of a colorless oil. The material was used without further purification.

Workup

  1. customThe solvent was removed in vacuo
  2. additiondiluted with dichloromethane
  3. washThe organic layer was washed (2×) with saturated NaHCO3 solution
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ee2822afbd764085929b1e0554d9fbb2
Source dataset
uspto-grants-2012_06
Patent number
US08202881B2

Reaction notes

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