Sodium 1,1,3,3,3-pentafluoro-2-hydroxypropane-1-sulfonate → 4-Fluorophenyldiphenylsulfonium 1,1,3,3,3-pentafluoro-2-hydroxypropanesulfonate
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]=1Participants
3
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
- extractionfollowed by twice extraction with 500 g of dichloromethane
- washThrough the steps of washing the organic layer with water
- distillationdistilling off the solvent in vacuum
- additionadding isopropyl ether
- customfor crystallization, filtration
- customdrying
- customthe target compound was obtained
Sources & evidence
- ORD record
- ord-46ec399a4dcf4a5e83a24652a9d09317
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173354B2
Reaction notes
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