Benzenesulfonyl chloride → 5-Fluoro-1-(phenylsulfonyl)-1H-indole

HRID 1895042Notes

Reaction equation

HRID 1895042 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.[OH-].[Na+].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[C:13]1([S:19]([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:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 678615-Fluoroindole

Product 1

HCID 112888585-Fluoro-1-(phenylsulfonyl)-1H-indoleYield 96%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

To a 0° C. solution of 5-fluoroindole (10 g, 74 mmol) and tetrabutyl ammonium hydrogen sulfate (3.8 g, 11 mmol) in 200 mL of toluene was added 200 mL 50% aqueous NaOH, followed by addition of benzene sulfonylchloride (14 mL, 111 mmol). The reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was extracted with ethyl acetate and washed with 1 M HCl, aqueous sodium bicarbonate, water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The remaining residue was recrystallized from ethyl acetate and hexanes to afford 19 g (96% yield) of 1-benzenesulfonyl-5-fluoro-1H-indole as a white crystalline solid.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with 1 M HCl, aqueous sodium bicarbonate, water and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe remaining residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-66b1cba5162448be8b4ec6930aaaafdd
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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