Trifluoroacetic anhydride → Diphenyl-p-tolylsulfonium perfluorooctanesulfonate

HRID 1265964

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:56])([S:52]([OH:55])(=[O:54])=[O:53])[C:30]([F:51])([F:50])[C:31]([F:49])([F:48])[C:32]([F:47])([F:46])[C:33]([F:45])([F:44])[C:34]([F:43])([F:42])[C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37]>C1(C)C=CC=CC=1>[F:56][C:29]([F:28])([S:52]([O-:55])(=[O:54])=[O:53])[C:30]([F:50])([F:51])[C:31]([F:49])([F:48])[C:32]([F:46])([F:47])[C:33]([F:45])([F:44])[C:34]([F:43])([F:42])[C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37].[CH3:36][C:35]1[CH:30]=[CH:31][C:32]([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:33][CH:34]=1

Participants

Conditions

Temperature: 2 °C

Procedure

Into a four-necked flask were charged 8.0 parts of diphenylsulfoxide and 80.0 parts of toluene, and the mixture was cooled to 2° C. Then, 16.6 parts of trifluoroacetic anhydride and 19.8 parts of perfluorooctanesulfonic acid were added and the mixture was stirred at the same temperature for 30 minutes. After standing, the lower layer was concentrated and diluted with 340 parts of chloroform. The obtained chloroform solution was washed six times with 85 parts of ion-exchange water and concentrated to give 27.7 parts of 4-methylphenyldiphenylsulfonium perfluorooctanesulfonate, which is referred to herein as PAG3.

Workup

concentrationthe lower layer was concentrated
additiondiluted with 340 parts of chloroform
washThe obtained chloroform solution was washed six times with 85 parts of ion-exchange water
concentrationconcentrated

Sources & evidence

ORD record: ord-e291b3deeda3401d959cef567596a5b2
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548221B2

Linked notes

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