Acetic Acid → 63166-90-5

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

Reactant 4

HCID 176Acetic Acid

HCID 784Hydrogen Peroxide

HCID 962Water

HCID 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

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

Sources & evidence

ORD record: ord-72bc35aa0a3d411a9bc72b57be17d7ba
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362016B2

Reaction notes

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