Hydrochloric Acid → Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonate

HRID 558046Notes

Reaction equation

HRID 558046 reaction equation
C([O:7][CH2:8][C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:12])=[O:11])(=O)C(C)(C)C.[C:16]1([S+:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].Cl>CO>[F:14][C:9]([F:15])([S:10]([O-:13])(=[O:12])=[O:11])[CH2:8][OH:7].[C:29]1([S+:22]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86632753Triphenylsulfonium 2-pivaloyloxy-1,1-difluoroethanesulfonate

Product 1

HCID 86632756Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonateYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triphenylsulfonium 2-(pivaloyloxy)-1,1-difluoroethanesulfonate, 243.5 g (0.48 mol), was dissolved in 760 g of methanol and ice cooled. A sodium hydroxide solution (40 g of sodium hydroxide in 120 g of water) was added dropwise to the solution at a temperature below 5° C. It was aged at room temperature for 8 hours. At a temperature below 10° C., dilute hydrochloric acid (99.8 g of 12N hydrochloric acid in 200 g of water) was added to the mixture to quench the reaction. Methanol was distilled off in vacuum, after which 1,000 g of dichloromethane was added to the residue. The organic layer was washed three times with 30 g of saturated sodium chloride water. The organic layer was concentrated, after which 1 L of diisopropyl ether was added to the concentrate for crystallization. The crystals were filtered and dried, obtaining the target compound. 187 g (purity 78%, net yield 78%).

Workup

  1. temperatureice cooled
  2. customto quench
  3. customthe reaction
  4. distillationMethanol was distilled off in vacuum
  5. additionafter which 1,000 g of dichloromethane was added to the residue
  6. washThe organic layer was washed three times with 30 g of saturated sodium chloride water
  7. concentrationThe organic layer was concentrated
  8. additionafter which 1 L of diisopropyl ether was added to the
  9. concentrationconcentrate for crystallization
  10. filtrationThe crystals were filtered
  11. customdried
  12. customobtaining the target compound

Sources & evidence

ORD record
ord-0e02b81abd0f4505bf575f1f4e2ebe44
Source dataset
uspto-grants-2011_11
Patent number
US08062828B2

Reaction notes

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