m-Chloroperbenzoic acid → 2-[1-[(4-Chlorophenyl)sulfonyl]-2-methyl-5-(methylsulfinyl)pentyl]-1,4-difluorobenzene

HRID 748698Notes

Reaction equation

HRID 748698 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][S:16][CH3:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:35])C=1>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[CH:12]([CH3:18])[CH2:13][CH2:14][CH2:15][S:16]([CH3:17])=[O:35])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 597507052-[1-[(4-Chlorophenyl)sulfonyl]-2-methyl-5-(methylthio)pentyl]-1,4-difluorobenzene

Product 1

HCID 597507102-[1-[(4-Chlorophenyl)sulfonyl]-2-methyl-5-(methylsulfinyl)pentyl]-1,4-difluorobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-[1-[(4-chlorophenyl)sulfonyl]-2-methyl-5-(methylthio)pentyl]-1,4-difluorobenzene (Isomer 43-A) (180 mg, 0.430 mmol) obtained in Example 43 was dissolved in methylene chloride (10 ml). Under ice cooling, 3-chloroperbenzoic acid (89 mg, 0.52 mmol) was added, followed by stirring at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was purified by silica gel chromatography (methylene chloride:methanol=40:1), whereby the title compound (172 mg, 92%) was obtained a colorless oil.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customwas purified by silica gel chromatography (methylene chloride:methanol=40:1), whereby the title compound (172 mg, 92%)
  4. customwas obtained a colorless oil

Sources & evidence

ORD record
ord-6c265e641e90460281c0331bde401710
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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