m-Chloroperbenzoic acid → HCID 59750823, compound

HRID 748796Notes

Reaction equation

HRID 748796 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH2:12][CH2:13][S:14][CH2:15][CH2:16][OH:17])(=[O:10])=[O:9])=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:34])C=1>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[CH2:12][CH2:13][S:14]([CH2:15][CH2:16][OH:17])=[O:34])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 59750752HCID 59750752, compound

Product 1

HCID 59750823HCID 59750823, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 2-[3-[(4-chlorophenyl)sulfonyl]-3-(2,5-difluorophenyl)propylthio]ethanol (65 mg, 0.16 mmol) obtained in Example 250 was dissolved in dichloromethane (5 ml), followed by the addition of 3-chloroperbenzoic acid (33 mg, 0.19 mmol) under ice cooling. The resulting mixture was stirred at room temperature for 14 hours. The residue obtained by concentrating the reaction mixture under reduced pressure was subjected to flash silica gel chromatography, and the fraction obtained from the dichloromethane:methanol=30:1 eluate was concentrated under reduced pressure to give a white solid. The white solid was washed with diethyl ether, whereby the title, compound (50 mg, 0.12 mmol, 74%) was obtained as a white powder.

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. customthe fraction obtained from the dichloromethane
  4. concentrationmethanol=30:1 eluate was concentrated under reduced pressure
  5. customto give a white solid
  6. washThe white solid was washed with diethyl ether, whereby the title

Sources & evidence

ORD record
ord-c72eefbb9aab4915abbaf2d6bad1cf99
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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