Triphenylsulfonium chloride → HCID 86638824, compound

HRID 2088299Notes

Reaction equation

HRID 2088299 reaction equation
[C:1]([O:7][CH2:8][C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:12])=[O:11])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[Na+].[Cl-].[C:18]1([S+:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O>[C:1]([O:7][CH2:8][C:9]([F:15])([F:14])[S:10]([O-:13])(=[O:11])=[O:12])(=[O:6])[CH2:2][CH2:3][CH2:4][CH3:5].[C:31]1([S+:24]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

4

Reactant 2

HCID 61343Triphenylsulfonium chloride2×HCID 59185162HCID 59185162, compound

Product 1

HCID 86638824HCID 86638824, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL reactor was charged with 3.0 g (purity 26%, 2.9 millimoles) of sodium 2-valeryloxy-1,1-difluoroethanesulfonate and 30 g of water, followed by adding dropwise an aqueous solution of triphenylsulfonium chloride [17.8 g (5.2 millimoles/1.8 equivalents) of triphenylsulfonium chloride and 16.2 g of water] at room temperature, followed by stirring at room temperature for 1.5 hours. Then, extraction was conducted by adding 30 mL of chloroform. The obtained organic layer was washed two times with water, followed by distilling solvent off, thereby obtaining 0.96 g of the target triphenylsulfonium 2-valeryloxy-1,1-difluoroethanesulfonate. Upon this, purity was 98%, and yield was 64%.

Workup

  1. extractionThen, extraction
  2. additionby adding 30 mL of chloroform
  3. washThe obtained organic layer was washed two times with water
  4. distillationby distilling solvent off,

Sources & evidence

ORD record
ord-252743217c8d4110ac6cb104b20895cc
Source dataset
uspto-grants-2013_05
Patent number
US08435717B2

Reaction notes

Loading…