Water → Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate

HRID 1515390Notes

Reaction equation

HRID 1515390 reaction equation
[OH:1][CH2:2][C:3]([F:9])([F:8])[S:4]([O-:7])(=[O:6])=[O:5].[Na+].O.[Cl-].[C:13]1([S+:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)(Cl)Cl>[OH:1][CH2:2][C:3]([F:9])([F:8])[S:4]([O-:7])(=[O:6])=[O:5].[C:26]1([S+:19]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 962WaterHCID 61343Triphenylsulfonium chloride5×HCID 25230669HCID 25230669, compound2×

Product 1

HCID 86632756Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonateYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 2 L reactor was charged with 183.7 g (38% purity, 0.38 mole) of sodium 2-hydroxy-1,1-difluoroethanesulfonate, 300 mL of water, 450 mL of chloroform and an aqueous solution of triphenylsulfonium chloride [142.8 g (0.49 mole/1.25 equivalents) of triphenylsulfonium chloride and 150 mL of water], followed by stirring at room temperature for 1 hour. A reaction solution was analyzed by using nuclear magnetic resonance (NMR), by which there was found almost half raw material sodium 2-hydroxy-1,1-difluoroethanesulfonate remaining. Accordingly, the reactor was further charged with an aqueous solution of triphenylsulfonium chloride [142.8 g (0.49 mole/1.25 equivalents) of triphenylsulfonium chloride and 150 mL of water], followed by stirring at room temperature for 0.5 hour (triphenylsulfonium chloride was used in an amount of 285.7 g (0.96 mole/2.5 equivalents) in total and the reaction time was 1.5 hours in total.). The reaction solution was analyzed by using nuclear magnetic resonance (NMR), by which the raw material was detected being consumed. Thereafter, the reaction solution was separated. The obtained water layer was extracted three times with 100 mL of chloroform while distilling a solvent out of the obtained organic layer, thereby obtaining 328.2 g of the target triphenylsulfonium 2-hydroxy-1,1-difluoroethanesulfonate. In this case, purity was 48% and yield was 97%.

Workup

  1. waitthe reaction time was 1.5 hours
  2. customby which the raw material was detected being consumed
  3. customThereafter, the reaction solution was separated
  4. extractionThe obtained water layer was extracted three times with 100 mL of chloroform
  5. distillationwhile distilling a solvent out of the obtained organic layer

Sources & evidence

ORD record
ord-370eefe4b65c4b3a99f99555b7b03a55
Source dataset
uspto-grants-2012_07
Patent number
US08222448B2

Reaction notes

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