m-Chloroperbenzoic acid → (3-(2,4-Dichlorophenyl)phenyl]isopropyl sulfoxide

HRID 25292Notes

Reaction equation

HRID 25292 reaction equation
[CH:1]([S:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[CH:6]=1)([CH3:3])[CH3:2].ClC1C=CC=C(C(OO)=[O:27])C=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH:1]([S:4]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[CH:6]=1)=[O:27])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22170929[3-(2,4-Dichlorophenyl)phenyl]isopropyl sulfide

Product 1

HCID 22170881(3-(2,4-Dichlorophenyl)phenyl]isopropyl sulfoxideYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 1.0 g (3.4 mmol) of [3-(2,4-dichlorophenyl)phenyl] isopropyl sulfide in 50 ml of chloroform, 0.7 g (4.1 mmol) of m-chloroperbenzoic acid was added at 0° C. with stirring, and the reaction mixture was stirred for 2 hours. The reaction mixture was stirred at room temperature for another 12 hours, and 5% aqueous sodium bicarbonate was added for separation. The chloroform layer was washed with 5% aqueous sodium sulfite and water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.9 g of [3-(2,4-dichlorophenyl)phenyl] isopropyl sulfoxide (yield 85.0%) as a colorless dough (nD20 1.6169).

Workup

  1. stirringthe reaction mixture was stirred for 2 hours
  2. stirringThe reaction mixture was stirred at room temperature for another 12 hours
  3. washThe chloroform layer was washed with 5% aqueous sodium sulfite and water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-a01dab6ea4d843dabe1a8911f5773857
Source dataset
uspto-grants-2005_02
Patent number
US06858639B2

Reaction notes

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