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m-Chloroperbenzoic acid → 3-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl ester

HRID 1367473
Notes
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Reaction equation

HRID 1367473 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7](SC2C=CC=CC=2Cl)[CH2:6]1)=[O:4].[CH:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[C:20](C(OO)=O)[CH:19]=1.[S:29](=[O:32])(O)[O-:30].[Na+]>ClCCl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][CH2:8][CH:7]([S:29]([C:23]2[CH:18]=[CH:19][CH:20]=[CH:21][C:22]=2[Cl:24])(=[O:32])=[O:30])[CH2:6]1)=[O:4]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 23665763Sodium BisulfiteHCID 669185443-(2-Chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester

Product 1

HCID 669185503-(2-Chloro-benzenesulfonyl)-cyclopentanecarboxylic acid methyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent
2×

Conditions

Temperature
0 °C

Procedure

A solution of 3-(2-chloro-phenylsulfanyl)-cyclopentanecarboxylic acid methyl ester (0.24 g, 1.0 eq) in dichloromethane (10 mL) was treated at 0° C. with a solution of MCPBA (1.1 g, 5.0 eq) in dichloromethane (7 mL), which was added dropwise. The mixture was stirred at 0° C. for 3 h, then treated with 20% sodium bisulfite and stirred at RT for 15 min. The mixture was filtered, washing with chloroform. The organic phase was washed with saturated sodium bicarbonate, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient, yielding the title compound as a colorless oil (0.25 g, 90%). MS (ESI): m/z=303.2 [M+H]+.

Workup

  1. additionwas added dropwise
  2. stirringstirred at RT for 15 min
  3. filtrationThe mixture was filtered
  4. washwashing with chloroform
  5. washThe organic phase was washed with saturated sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe residue was purified by flash chromatography on silica gel with a heptane/ethyl acetate gradient

Sources & evidence

ORD record
ord-bc2ad3f332d74e68afdee6e6971481d1
Source dataset
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07893099B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes