Bromine → 1-benzenesulfonyl-3-bromo-7-fluoro-1H-indole

HRID 1692883Notes

Reaction equation

HRID 1692883 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[Br:25]Br>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl.O>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[F:19])[C:12]([Br:25])=[CH:11]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

7

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 116877057-Fluoro-1-(phenylsulfonyl)-1H-indole

Product 1

HCID 596035291-benzenesulfonyl-3-bromo-7-fluoro-1H-indoleYield 95%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzenesulfonyl-7-fluoro-1H-indole (1.00 g, 3.63 mmol) in CCl4 (20 mL) was added a solution of saturated sodium bicarbonate (40 mL) and bromine (0.19 mL, 3.81 mmol) at room temperature. After stirring at room temperature for 16 hours, the reaction was diluted with DCM and water. The organic extract was washed with saturated sodium bicarbonate, 10% aqueous sodium thiosulfate, dried over sodium sulfate, filtered, and concentrated. The product was obtained as an off-white solid (1.22 g, 95%)

Workup

  1. extractionThe organic extract
  2. washwas washed with saturated sodium bicarbonate, 10% aqueous sodium thiosulfate
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3c5862e76e3f4feb971f97f09d7bf6a5
Source dataset
uspto-grants-2012_04
Patent number
US08158625B2

Reaction notes

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