Toluene → 1-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole

HRID 1793868Notes

Reaction equation

HRID 1793868 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH-].[Na+].C1(C)C=CC=CC=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH:5]=[CH:6]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 73984-Chlorobenzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 678615-Fluoroindole

Product 1

HCID 222201261-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indoleYield 75.9%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolvent

Procedure

A mixture of 5-fluoroindole (1.0 g, 7.4 mmole), 4-chlorobenzenesulfonyl chloride (1.6 g, 7.6 mmole), tetra-n-butylammonium hydrogen sulfate (0.05 g), 4N sodium hydroxide (5 mL, 20 mmol), and toluene (6 mL) was stirred at room temperature for 15 h. The mixture was diluted with 10 mL water and extracted with 25 mL ethyl acetate. The organic phase was washed with 10 mL water, 10 mL saturated sodium chloride, and then dried (anhydrous magnesium sulfate). The solution was concentrated under reduced pressure. The residue was recrystallized from ethyl ether/hexane to provide 1-(4-Chlorobenzenesulfonyl)-5-fluoro-1H-indole (1.74 g) m.p. 108–109°.

Workup

  1. extractionextracted with 25 mL ethyl acetate
  2. washThe organic phase was washed with 10 mL water, 10 mL saturated sodium chloride
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. concentrationThe solution was concentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl ether/hexane

Sources & evidence

ORD record
ord-616b2c0f6a604a29b66a75f3e1e10247
Source dataset
uspto-grants-2006_04
Patent number
US07022708B2

Reaction notes

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