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

HRID 1914061Notes

Reaction equation

HRID 1914061 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

Triphenylsulfonium 2-(pivaloyloxy)-1,1-difluoroethane-sulfonate, 50.9 g (0.1 mole), was dissolved in 200 g of methanol and ice cooled. 2.0 g of a 28 wt % methanol solution of sodium methoxide was added. The solution was allowed to mature for 24 hours at room temperature. At a temperature below 10° C., 1.0 g of 12N hydrochloric acid was added to quench the reaction. The methanol was distilled off in vacuum. To the residue was added 250 g of dichloromethane. The inorganic salt was filtered off, after which 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. Amount 42 g (purity 99%, reduced yield 99%).

Workup

  1. temperatureice cooled
  2. customto quench
  3. customthe reaction
  4. distillationThe methanol was distilled off in vacuum
  5. additionTo the residue was added 250 g of dichloromethane
  6. filtrationThe inorganic salt was filtered off
  7. concentrationafter which the filtrate was concentrated
  8. additionDiisopropyl ether, 150 g, 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-6719c0c6310f4b5989df74c34ecbf7ef
Source dataset
uspto-grants-2013_12
Patent number
US08609889B2

Reaction notes

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