Benzenesulfonyl chloride → 4-Bromo-1-(phenylsulfonyl)-1H-indole

HRID 1159794Notes

Reaction equation

HRID 1159794 reaction equation
[H-].[Na+].C1COCC1.[Br:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][NH:13]2.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCCCCCC.CCOC(C)=O.O>[Br:8][C:9]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:10]=1[CH:11]=[CH:12][N:13]2[S:24]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(=[O:26])=[O:25]

Participants

8

Reactant 4

HCID 7369Benzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydride2×HCID 6764944-Bromoindole

Product 1

HCID 220153114-Bromo-1-(phenylsulfonyl)-1H-indoleYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 8900HeptaneSolvent

Procedure

Sodium hydride (2.8 g, 60%, 70.4 mmol) was washed with heptane to remove the mineral oil prior reaction. The sodium hydride was mixed with THF (250 mL) and cooled on an ice bath before 4-bromoindole (4.6 g, 23.5 mmol) was added. The reaction mixture was stirred for 15 minutes before benzenesulfonyl chloride (6.22 g, 35.2 mmol) was added. The reaction mixture was stirred at RT ON. Ice and water was added followed by EtOAc. The phases were separated and the aqueous phase was extracted with EtOAc twice. The combined organic phases were dried (MgSO4) before the solvent was evaporated. The obtained crude product was pure enough to be used in the next step. Got 8.52 g of an oil which solidified on standing, yield 100%. MS (ESI+) for C14H10BrNO2S m/z 336 (M+H)+.

Workup

  1. customto remove the mineral oil
  2. customreaction
  3. additionwas added
  4. additionwas added
  5. customThe phases were separated
  6. extractionthe aqueous phase was extracted with EtOAc twice
  7. dry with materialThe combined organic phases were dried (MgSO4) before the solvent
  8. customwas evaporated
  9. customThe obtained crude product

Sources & evidence

ORD record
ord-a4f1699f7b9b4b6f96e47fd451ec1267
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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