Water → Triphenylsulfonium 4-hydroxy-1,1,2,2-tetrafluorobutanesulfonate

HRID 2421456Notes

Reaction equation

HRID 2421456 reaction equation
[F:1][C:2]([F:13])([S:9]([O-:12])(=[O:11])=[O:10])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6].[Na+].[Cl-].[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.O>ClCCl>[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.[F:13][C:2]([F:1])([S:9]([O-:12])(=[O:11])=[O:10])[C:3]([F:8])([F:7])[CH2:4][CH2:5][OH:6]

Participants

5

Reactant 3

HCID 962WaterHCID 61343Triphenylsulfonium chlorideHCID 58463092Sodium 1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfonate

Product 1

HCID 86639888Triphenylsulfonium 4-hydroxy-1,1,2,2-tetrafluorobutanesulfonateYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using a 2 litter reactor, 121 g of sodium 1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfonate (purity 78%, 0.38 mol) obtained in the second step was suspended in 560 g of dichloromethane. An aqueous solution of triphenylsulfonium chloride (115 g of triphenylsulfonium chloride (0.385 mol/1.01 equivalent)) and 450 g of water) was added dropwise to the suspension at room temperature. The resulting reaction solution separated in two layers was vigorously stirred at room temperature for 90 minutes to separate the organic layer. The organic layer was washed four times with 250 ml of water. Volatile components were removed from the organic layer by distillation and the residue was dried to solidify to obtain 167 g of the target triphenylsulfonium-1,1,2,2-tetrafluoro-4-hydroxybutane-1-sulfonate. The purity of the product was 97% and the yield was 93%.

Workup

  1. customobtained in the second step
  2. customThe resulting reaction solution
  3. customseparated in two layers
  4. customto separate the organic layer
  5. washThe organic layer was washed four times with 250 ml of water
  6. customVolatile components were removed from the organic layer by distillation
  7. customthe residue was dried

Sources & evidence

ORD record
ord-572932ba4a3f41c49b46879eecf67550
Source dataset
uspto-grants-2011_06
Patent number
US07956142B2

Reaction notes

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