Toluene → Diphenyl(4-methylphenyl)sulfonium nonafluorobutanesulfonate

HRID 1265965

Reaction equation

HRID 1265965 reaction equation
[C:1]1([S:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:28][C:29]([F:44])([S:40]([OH:43])(=[O:42])=[O:41])[C:30]([F:39])([F:38])[C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33].[C:45]1([CH3:51])[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>>[F:44][C:29]([F:28])([S:40]([O-:43])(=[O:42])=[O:41])[C:30]([F:38])([F:39])[C:31]([F:37])([F:36])[C:32]([F:35])([F:34])[F:33].[CH3:51][C:45]1[CH:50]=[CH:49][C:48]([S+:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:47][CH:46]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 9845Trifluoroacetic anhydrideHCID 13679Diphenyl sulfoxideHCID 67815Perfluorobutanesulfonic acid

Product 1

HCID 21863628Diphenyl(4-methylphenyl)sulfonium nonafluorobutanesulfonate

Conditions

Temperature
2 °C

Procedure

Into a four-necked flask were charged 5.06 parts of diphenylsulfoxide and 50.6 parts of toluene, and the mixture was cooled to 2° C. Then, 10.5 parts of trifluoroacetic anhydride and 7.50 parts of perfluorobutanesulfonic acid were added and the mixture was stirred at the same temperature for 60 minutes. After standing, the lower layer was concentrated and diluted with 100 parts of chloroform. The obtained chloroform solution was washed 11 times with 50 parts of ion-exchange water and concentrated to give 12.0 parts of 4-methylphenyldiphenylsulfonium perfluorobutanesulfonate, which is referred to herein as PAG4.

Workup

  1. concentrationthe lower layer was concentrated
  2. additiondiluted with 100 parts of chloroform
  3. washThe obtained chloroform solution was washed 11 times with 50 parts of ion-exchange water
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-85123cd818f34e1987949c06452d2efd
Source dataset
uspto-grants-2003_04
Patent number
US06548221B2

Linked notes

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