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

HRID 748700Notes

Reaction equation

HRID 748700 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][S:16]([CH3:18])=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:36])C=1.C(OCC)C.C(Cl)Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=2[F:27])[CH:12]([CH3:19])[CH2:13][CH2:14][CH2:15][S:16]([CH3:18])(=[O:36])=[O:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 21881112Ethyl ether methylene chlorideHCID 597507102-[1-[(4-Chlorophenyl)sulfonyl]-2-methyl-5-(methylsulfinyl)pentyl]-1,4-difluorobenzene

Product 1

HCID 597509062-[1-[(4-Chlorophenyl)sulfonyl]-2-methyl-5-(methylsulfonyl)pentyl]-1,4-difluorobenzeneYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-[1-[(4-chlorophenyl)sulfonyl]-2-methyl-5-(methylsulfinyl)pentyl]-1,4-difluorobenzene (76 mg, 0.18 mmol) obtained in Example 44 was dissolved in methylene chloride (5 ml). Under ice cooling, 3-chloroperbenzoic acid (36 mg, 0.21 mmol) was added. The resulting mixture was stirred at room temperature for 2 hours. The residue obtained by concentrating the reaction mixture was purified by silica gel chromatography (methylene chloride:methanol=100:1) to yield a pale yellowish brown oil. The resulting pale yellowish brown oil was solidified with diethyl ether/methylene chloride, whereby the title compound (61 mg, 77%) was obtained as a white powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture
  3. customwas purified by silica gel chromatography (methylene chloride:methanol=100:1)
  4. customto yield a pale yellowish brown oil

Sources & evidence

ORD record
ord-f84630a948704d949010d4d33e934bce
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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