Sodium Thiosulfate → Benzo[b]thiophene, 5-bromo-, 1,1-dioxide

HRID 521183Notes

Reaction equation

HRID 521183 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2S[CH:8]=[CH:7][C:6]=2[CH:10]=1.C1C=C(Cl)C=C(C(OO)=O)C=1.[S:22]([O-:26])([O-])(=[O:24])=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:22](=[O:26])(=[O:24])[CH:8]=[CH:7][C:6]=2[CH:10]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 27765785-Bromo-1-benzothiophene

Product 1

HCID 23261743Benzo[b]thiophene, 5-bromo-, 1,1-dioxide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Bromo-1-benzothiophene (1.50 g, 7.04 mmol) was dissolved in chloroform (47 mL) and allowed to stir vigorously at ambient temperature. m-CPBA (4.34 g, 17.6 mmol) was added in three portions and the resulting mixture was maintained at ambient temperature for 16 hours. The mixture was then diluted with 1M aqueous sodium thiosulfate and extracted with EtOAc. The organic layer was again washed with 1M aqueous sodium thiosulfate, saturated aqueous NaHCO3, brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The residue was purified by MPLC on silica gel (using a gradient elution of 0-30% EtOAc/hexanes). Desired fractions were identified, combined, and concentrated in vacuo to afford the title compound.

Workup

  1. temperaturethe resulting mixture was maintained at ambient temperature for 16 hours
  2. extractionextracted with EtOAc
  3. washThe organic layer was again washed with 1M aqueous sodium thiosulfate, saturated aqueous NaHCO3, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by MPLC on silica gel (
  8. washa gradient elution of 0-30% EtOAc/hexanes)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bccfe4394601415e95306fa85873f336
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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