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

HRID 424332Notes

Reaction equation

HRID 424332 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.C[O-].[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 10942334Sodium MethoxideHCID 86632753Triphenylsulfonium 2-pivaloyloxy-1,1-difluoroethanesulfonate

Product 1

HCID 86632756Triphenylsulfonium 1,1-difluoro-2-hydroxyethanesulfonateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 200 g of methanol was dissolved 50.9 g (0.1 mole) of triphenylsulfonium 2-(pivaloyloxy)-1,1-difluoroethane-sulfonate. To this solution under ice cooling, 2.0 g of a 28 wt % methanol solution of sodium methoxide was added. The reaction solution was allowed to mature at room temperature for 24 hours, and 1.0 g of 12N hydrochloric acid 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 250 g of dichloromethane. After the inorganic salt was filtered off, the filtrate was concentrated. Diisopropyl ether, 150 g, was added to the concentrate for crystallization. The crystals were filtered and dried, obtaining the target compound (PAG1), 42 g (purity 99%, net yield 99%).

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 250 g of dichloromethane
  5. filtrationAfter the inorganic salt was filtered off
  6. concentrationthe filtrate was concentrated
  7. additionDiisopropyl ether, 150 g, was added to the
  8. concentrationconcentrate for crystallization
  9. filtrationThe crystals were filtered
  10. customdried
  11. customobtaining the target compound (PAG1), 42 g (purity 99%, net yield 99%)

Sources & evidence

ORD record
ord-37b0cc3da1bd4311a1360817532e6a7e
Source dataset
uspto-grants-2012_01
Patent number
US08105748B2

Reaction notes

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