Bromine → 1-benzenesulfonyl-3-bromo-5-fluoro-1H-indole

HRID 503915Notes

Reaction equation

HRID 503915 reaction equation
[Br:1]Br.[C:3]1([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)(=[O:11])=[O:10])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[NH4+].[Cl-]>CN(C=O)C>[C:3]1([S:9]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([F:21])=[CH:18][CH:19]=3)[C:14]([Br:1])=[CH:13]2)(=[O:11])=[O:10])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 25517Ammonium ChlorideHCID 112888585-Fluoro-1-(phenylsulfonyl)-1H-indole

Product 1

HCID 594283491-benzenesulfonyl-3-bromo-5-fluoro-1H-indoleYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromine (0.187 mL, 3.632 mmol) was added dropwise to a room temperature solution of 1-benzenesulfonyl-5-fluoro-1H-indole (1.0 g, 3.632 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 5 hours. A saturated solution of NH4Cl was added, and the resulting mixture was extracted with EtOAc. The combined organic extracts were washed with water and with brine; dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 95/5) to give 0.676 g (53% yield) of 1-benzenesulfonyl-3-bromo-5-fluoro-1H-indole as a white solid.

Workup

  1. extractionthe resulting mixture was extracted with EtOAc
  2. washThe combined organic extracts were washed with water and with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified via flash chromatography (hexane/EtOAc, 95/5)

Sources & evidence

ORD record
ord-c329b5df67c946eb8a828aade75ee0d2
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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