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

HRID 1640362Notes

Reaction equation

HRID 1640362 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

In 760 g of methanol was dissolved 243.5 g (0.48 mole) of triphenylsulfonium 2-pivaloyloxy-1,1-difluoroethanesulfonate. To this solution under ice cooling, an aqueous solution of sodium hydroxide (40 g sodium hydroxide in 120 g water) was added dropwise at a temperature below 5° C. The reaction solution was aged at room temperature for 8 hours, and dilute hydrochloric acid (99.8 g 12N hydrochloric acid in 200 g water) was added thereto at a temperature below 10° C. to quench the reaction. The methanol was distilled off in vacuum. To the residue was added 1,000 g of dichloromethane. The organic layer was washed with 30 g of saturated saline three times and concentrated. Diisopropyl ether, 1 L, 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. customat a temperature below 10° C. to quench
  2. customthe reaction
  3. distillationThe methanol was distilled off in vacuum
  4. additionTo the residue was added 1,000 g of dichloromethane
  5. washThe organic layer was washed with 30 g of saturated saline three times
  6. concentrationconcentrated
  7. additionDiisopropyl ether, 1 L, was added to the
  8. concentrationconcentrate for crystallization
  9. filtrationThe crystals were filtered
  10. customdried
  11. customobtaining the target compound

Sources & evidence

ORD record
ord-b3b0ea6b11e046e496ff6ab989eeaa0f
Source dataset
uspto-grants-2012_02
Patent number
US08114570B2

Reaction notes

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