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

HRID 748699Notes

Reaction equation

HRID 748699 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-B) (175 mg, 0.418 mmol) obtained in Example 43 was dissolved in methylene chloride (10 ml). Under ice cooling, 3-chloroperbenzoic acid (87 mg, 0.50 mmol) was added. The resulting mixture was stirred at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was purified silica gel chromatography (methylene chloride:methanol=40:1) to yield a white solid. The resulting solid was washed with diethyl ether, whereby the title compound (118 mg, 65%) was obtained as a white powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customwas purified silica gel chromatography (methylene chloride:methanol=40:1)
  4. customto yield a white solid
  5. washThe resulting solid was washed with diethyl ether, whereby the title compound (118 mg, 65%)
  6. customwas obtained as a white powder

Sources & evidence

ORD record
ord-771c2f7a47844b40a954533bde97efde
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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