4-Toluenesulfonyl chloride → 5-fluoro-N-tosylindole

HRID 2381927Notes

Reaction equation

HRID 2381927 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.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.[OH-].[Na+]>C1(C)C=CC=CC=1.O.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:17]([C:14]1[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=1)(=[O:19])=[O:18])[CH:6]=[CH:5]2

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 678615-Fluoroindole

Product 1

HCID 167513275-fluoro-N-tosylindoleYield 92.6%

Reagents, catalysts & solvents 3

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of 5-fluoroindole (5.4 g) and toluene-4-sulphonyl chloride (9.12 g) in toluene (300 mL) is treated with a cooled solution of sodium hydroxide pellets (23.2 g) in water (200 mL) followed by the tetrabutylammonium hydrogen sulfate catalyst (400 mg). The mixture is stirred at rt for 24 h. The organic phase is separated, washed with water and brine, dried (MgSO4) and concentrated in vacuo to afford 5-fluoro-1-(toluene-4-sulfonyl)-1H-indole (10.7 g, 78%). MS: 290 (M+H)

Workup

  1. customThe organic phase is separated
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-715a3f7af4f2497c920f97a280e35922
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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