m-Chloroperbenzoic acid → 4-Oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-3-methylsulfinyl-4-pentafluorethylbenzoate

HRID 1910386Notes

Reaction equation

HRID 1910386 reaction equation
[CH3:1][C:2]1[C:19]([S:20][CH3:21])=[C:18]([C:22]([F:28])([F:27])[C:23]([F:26])([F:25])[F:24])[CH:17]=[CH:16][C:3]=1[C:4]([O:6][C:7]1[CH:8]2[CH2:15][CH:11]([C:12](=[O:14])[CH:13]=1)[CH2:10][CH2:9]2)=[O:5].ClC1C=CC=C(C(OO)=[O:37])C=1>ClCCl>[CH3:1][C:2]1[C:19]([S:20]([CH3:21])=[O:37])=[C:18]([C:22]([F:28])([F:27])[C:23]([F:25])([F:26])[F:24])[CH:17]=[CH:16][C:3]=1[C:4]([O:6][C:7]1[CH:8]2[CH2:15][CH:11]([C:12](=[O:14])[CH:13]=1)[CH2:10][CH2:9]2)=[O:5]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 866614334-Oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-3-methylthio-4-(pentafluoroethyl)benzoate

Product 1

HCID 871045914-Oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-3-methylsulfinyl-4-pentafluorethylbenzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

280 mg (90% by weight; 0.599 mmol) of 4-oxobicyclo[3.2.1]oct-2-en-2-yl 2-methyl-3-methylthio-4-pentafluoroethylbenzoate were introduced into 20 ml of dichloromethane and admixed with 134 mg (77% by weight; 0.599 mmol) of meta-chloroperbenzoic acid. The mixture was stirred at RT until monitoring of the reaction by thin-layer chromatography indicated complete conversion. For working up, the contents were washed once with 10% strength aqueous sodium hydrogensulfite solution, then twice with saturated aqueous sodium hydrogencarbonate solution. Finally, the organic phase was freed from the solvent. As the residue, 250 mg of product with a purity of 95% by weight were recovered.

Workup

  1. washthe contents were washed once with 10% strength aqueous sodium hydrogensulfite solution
  2. customAs the residue, 250 mg of product with a purity of 95% by weight were recovered

Sources & evidence

ORD record
ord-35965a8506ca402582ba4e96a619585a
Source dataset
uspto-grants-2013_12
Patent number
US08603947B2

Reaction notes

Loading…