Acetic Acid → 63166-90-5

HRID 549860Notes

Reaction equation

HRID 549860 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-f2e175698df6473ba764c1d5ae9143ad
Source dataset
uspto-grants-2011_05
Patent number
US07943613B2

Reaction notes

Loading…