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Sodium 1,1,3,3,3-pentafluoro-2-hydroxypropane-1-sulfonate → 4-Fluorophenyldiphenylsulfonium 1,1,3,3,3-pentafluoro-2-hydroxypropanesulfonate

HRID 1920614
Notes
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Reaction equation

HRID 1920614 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.[F:22][C:23]([F:34])([S:30]([O-:33])(=[O:32])=[O:31])[CH:24]([OH:29])[C:25]([F:28])([F:27])[F:26].[Na+]>>[F:34][C:23]([F:22])([S:30]([O-:33])(=[O:31])=[O:32])[CH:24]([OH:29])[C:25]([F:26])([F:28])[F:27].[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 86612200Sodium 1,1,3,3,3-pentafluoro-2-hydroxypropane-1-sulfonateHCID 866496604-Fluorophenyldiphenylsulfonium chloride

Product 1

HCID 866496594-Fluorophenyldiphenylsulfonium 1,1,3,3,3-pentafluoro-2-hydroxypropanesulfonateYield 70%

Procedure

An amount (0.2 mole) of the 4-fluorophenyldiphenyl-sulfonium chloride aqueous solution in Synthesis Example 1 was combined with an amount (0.2 mole) of the sodium 1,1,3,3,3-pentafluoro-2-hydroxypropanesulfonate aqueous solution in Synthesis Example 2, followed by twice extraction with 500 g of dichloromethane. Through the steps of washing the organic layer with water, distilling off the solvent in vacuum, adding isopropyl ether for crystallization, filtration and drying, the target compound was obtained. White crystals, 71.5 g, yield 70% (based on diphenyl sulfoxide).

Workup

  1. extractionfollowed by twice extraction with 500 g of dichloromethane
  2. washThrough the steps of washing the organic layer with water
  3. distillationdistilling off the solvent in vacuum
  4. additionadding isopropyl ether
  5. customfor crystallization, filtration
  6. customdrying
  7. customthe target compound was obtained

Sources & evidence

ORD record
ord-46ec399a4dcf4a5e83a24652a9d09317
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08173354B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes