Acetic Acid → 63166-90-5

HRID 1039476Notes

Reaction equation

HRID 1039476 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6][C:7]([CH3:9])=[CH:8][C:4]=2[CH:3]=1.OO.[OH2:14].C(O)(=[O:17])C>>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[S:6](=[O:17])(=[O:14])[C:7]([CH3:9])=[CH:8][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 962WaterHCID 136630355-Bromo-2-methyl-1-benzothiophene

Product 1

HCID 1234629763166-90-5

Procedure

5-Bromo-2-methylbenzo[b]thiophene (8.0 g, 35.2 mmol; prepared according to J. Med. Chem. 1986, 29, 1643) was dissolved in acetic acid (200 mL); 30% hydrogen peroxide (50 mL) was added and the mixture was refluxed for 4 h. Water (500 mL) was added and the mixture was extracted with benzene (300 mL). The organic layer was evaporated in vacuo and the residue was purified by column chromatography (silica gel Fluka 60, benzene) affording 5-bromo-2-methylbenzo[b]thiophene-1,1-dioxide.

Workup

  1. temperaturethe mixture was refluxed for 4 h
  2. extractionthe mixture was extracted with benzene (300 mL)
  3. customThe organic layer was evaporated in vacuo
  4. customthe residue was purified by column chromatography (silica gel Fluka 60, benzene)

Sources & evidence

ORD record
ord-587778ccf4c24ad690e7493d8eea9adf
Source dataset
uspto-grants-2013_10
Patent number
US08551993B2

Reaction notes

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