Toluene → 1-(Benzenesulfonyl)-5-bromo-1H-indole

HRID 1279383Notes

Reaction equation

HRID 1279383 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C1(C)C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[C:18]1([S:24]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Br:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 7369Benzenesulfonyl chlorideHCID 249055-Bromoindole

Product 1

HCID 27762101-(Benzenesulfonyl)-5-bromo-1H-indoleYield 91.1%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-bromoindole (5 g, 25.5 mmol) and tetra-n-butylammonium hydrogen sulfate (866 mg, 2.55 mmol) in 50% NaOE (50 mL) and toluene (200 mL) is stirred at room temperature for 5 min. Benzenesulfonyl chloride (3.57 mL, 28 mmol) is added and the mixture stirred for 1 hr. The mixture is diluted with water (500 mL) and extracted with EtOAc (3×100 mL). The extracts are washed with brine (250 mL), dried over MgSO4, filtered and evaporated to a yellow oil. The oil is purified by medium-pressure column chromatography on silica gel eluting with 10% EtOAc/hexanes to give the title compound as a white solid (7.81 g).

Workup

  1. stirringthe mixture stirred for 1 hr
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe extracts are washed with brine (250 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated to a yellow oil
  7. customThe oil is purified by medium-pressure column chromatography on silica gel eluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-97b58f37bfb04a96b9268c60920b5fc2
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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