Hydrogen Peroxide → HCID 22220124, compound

HRID 1793872Notes

Reaction equation

HRID 1793872 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1.OO.C(=O)([O-])[O-:22].[Na+].[Na+].[OH2:27]>C(O)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[S:11]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:22])=[O:27]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 10340Sodium CarbonateHCID 22220127HCID 22220127, compound

Product 1

HCID 22220124HCID 22220124, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The 5-Bromo-3-(4-fluoro-phenylsulfanyl)-1H-indole (1.34 g, 4.16 mmol) from Step 1 was suspended in formic acid (20 mL). To this was added 30% hydrogen peroxide (0.94 g, 8.3 mmole). The reaction mixture was stirred at room temperature for 1 hour. The mixture was diluted with 80 mL water and extracted with 100 mL ethyl acetate. The organic phase was washed with 1.5M sodium carbonate (20 mL, 30 mmol), dried (magnesium sulfate), and concentrated under reduced pressure. The residue was recrystallized from ether/hexane to provide 5-Bromo-3-(4-fluoro-benzenesulfonyl)-1H-indole (1.4 g, 4.0 mmol), m.p. 163–164°.

Workup

  1. extractionextracted with 100 mL ethyl acetate
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was recrystallized from ether/hexane

Sources & evidence

ORD record
ord-e5f89e0972404067afff2b2cad0d8d20
Source dataset
uspto-grants-2006_04
Patent number
US07022708B2

Reaction notes

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