p-Toluenesulfonic acid monohydrate → 4-Fluorophenyldiphenylsulfonium 4-toluene-sulfonate

HRID 1920615Notes

Reaction equation

HRID 1920615 reaction equation
[Cl-].[F:2][C:3]1[CH:8]=[CH:7][C:6]([S+:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>>[C:23]1([CH3:33])[CH:24]=[CH:25][C:26]([S:29]([O-:32])(=[O:30])=[O:31])=[CH:27][CH:28]=1.[F:2][C:3]1[CH:8]=[CH:7][C:6]([S+:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 866496604-Fluorophenyldiphenylsulfonium chloride

Product 1

HCID 187593244-Fluorophenyldiphenylsulfonium 4-toluene-sulfonate

Procedure

The 4-fluorophenyldiphenylsulfonium chloride aqueous solution in Synthesis Example 1 was combined with 4-toluenesulfonic acid monohydrate, followed by extraction with dichloromethane. The organic layer was washed with water, after which the solvent was distilled off in vacuum. Isopropyl ether was added to the residue for crystallization. Filtration and drying yielded the target compound.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with water
  3. distillationafter which the solvent was distilled off in vacuum
  4. additionIsopropyl ether was added to the residue for crystallization
  5. filtrationFiltration
  6. customdrying
  7. customyielded the target compound

Sources & evidence

ORD record
ord-e4d0aa0b8d964600aea8289334b6cc85
Source dataset
uspto-grants-2012_05
Patent number
US08173354B2

Reaction notes

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