Chloroform → Bis(triphenylsulfonium) perfluorobutane-1,4-disulfonate

HRID 414881Notes

Reaction equation

HRID 414881 reaction equation
[K+].[F:2][C:3]([F:21])([S:17]([O-:20])(=[O:19])=[O:18])[C:4]([F:16])([F:15])[C:5]([F:14])([F:13])[C:6]([F:12])([F:11])[S:7]([O-:10])(=[O:9])=[O:8].[K+].[Br-].[C:24]1([S+:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(Cl)(Cl)Cl>O>[F:12][C:6]([F:11])([S:7]([O-:10])(=[O:9])=[O:8])[C:5]([F:14])([F:13])[C:4]([F:15])([F:16])[C:3]([F:2])([F:21])[S:17]([O-:20])(=[O:18])=[O:19].[C:37]1([S+:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1.[C:37]1([S+:30]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 11984010Triphenylsulfonium BromideHCID 14384439Perfluorobutane-1,4-disulfonic acid potassium salt

Product 1

HCID 87079447Bis(triphenylsulfonium) perfluorobutane-1,4-disulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Perfluorobutane-1,4-disulfonic acid potassium salt (2.5 g) was added to a solution of triphenylsulfonium bromide (3.5 g) in 150 ml of water. Chloroform (150 ml) was added and stirred for 5 hours. The chloroform layer was washed several times with water, dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to an oil stage. Ether was added to the oil and the mixture was stirred vigorously. A white precipitate formed. The mixture was filtered and recovered precipitate was dried under vacuum, resulting in a white powder; mp 155° C.

Workup

  1. washThe chloroform layer was washed several times with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe filtrate evaporated to an oil stage
  5. additionEther was added to the oil
  6. stirringthe mixture was stirred vigorously
  7. customA white precipitate formed
  8. filtrationThe mixture was filtered
  9. customrecovered precipitate
  10. customwas dried under vacuum
  11. customresulting in a white powder

Sources & evidence

ORD record
ord-5a8415d00d4646b4972e7d00f9d6914e
Source dataset
uspto-grants-2012_01
Patent number
US08088548B2

Reaction notes

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