m-Chloroperbenzoic acid → 1-(Cyclopentylsulfonyl)-3-iodo-5-methylbenzene

HRID 2118343Notes

Reaction equation

HRID 2118343 reaction equation
C1(S[C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([I:14])[CH:8]=2)CCCC1.ClC1C=[C:18]([CH:23]=[CH:24][CH:25]=1)[C:19](OO)=O.[S:26](S([O-])=O)([O-:29])(=O)=[O:27].[Na+].[Na+]>C(Cl)Cl>[CH:19]1([S:26]([C:7]2[CH:12]=[C:11]([CH3:13])[CH:10]=[C:9]([I:14])[CH:8]=2)(=[O:29])=[O:27])[CH2:18][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 691197121-(Cyclopentylthio)-3-iodo-5-methylbenzene

Product 1

HCID 691200091-(Cyclopentylsulfonyl)-3-iodo-5-methylbenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(cyclopentylthio)-3-iodo-5-methylbenzene (440 mg) in DCM (20 ml) at 20° under nitrogen was treated with 3-chloroperoxybenzoic acid (1.046 g, 57-86% pure) and the mixture stirred at 20° for 2 h. 0.5M Aqueous sodium metabisulphite solution was added and the mixture was vigorously stirred at 20° for 18 h. The layers were separated and the organic phase washed with 0.5M aqueous sodium metabisulphite solution. The organic phase was dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified using a SPE bond elut cartridge (2×10 g, silica). Elution with DCM (5 vols) gave the title compound (425 mg). LCMS RT=3.36 min.

Workup

  1. stirringthe mixture was vigorously stirred at 20° for 18 h
  2. customThe layers were separated
  3. washthe organic phase washed with 0.5M aqueous sodium metabisulphite solution
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified
  7. washElution with DCM (5 vols)

Sources & evidence

ORD record
ord-1f806022ec424e8d918432ebc559b3ce
Source dataset
uspto-grants-2008_10
Patent number
US07442839B2

Reaction notes

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