Triphenylsulfonium Bromide → Bis (4-t-butylphenyl iodonium) triphenyl sulfonium perfluorobutane-1,4-disulfonate

HRID 1172026Notes

Reaction equation

HRID 1172026 reaction equation
[Br-].[C:2]1([S+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C.[C:25]([C:29]1[CH:34]=[CH:33][C:32]([IH+:35])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26].[C:36]([C:40]1[CH:45]=[CH:44][C:43]([IH+:46])=[CH:42][CH:41]=1)([CH3:39])([CH3:38])[CH3:37].C([O-])(=O)C.[F:51][C:52]([F:70])([S:66]([OH:69])(=[O:68])=[O:67])[C:53]([F:65])([F:64])[C:54]([F:63])([F:62])[C:55]([F:61])([F:60])[S:56]([OH:59])(=[O:58])=[O:57]>O.CC(C)=O>[F:61][C:55]([F:60])([S:56]([O-:59])(=[O:58])=[O:57])[C:54]([F:63])([F:62])[C:53]([F:64])([F:65])[C:52]([F:51])([F:70])[S:66]([O-:69])(=[O:67])=[O:68].[C:15]1([S+:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1.[C:25]([C:29]1[CH:30]=[CH:31][C:32]([IH+:35])=[CH:33][CH:34]=1)([CH3:28])([CH3:26])[CH3:27].[C:36]([C:40]1[CH:41]=[CH:42][C:43]([IH+:46])=[CH:44][CH:45]=1)([CH3:39])([CH3:37])[CH3:38]

Participants

6

Reactant 3

HCID 11984010Triphenylsulfonium BromideHCID 138480021,4-Butanedisulfonic acid, 1,1,2,2,3,3,4,4-octafluoro-HCID 131728420Bis (4-t-butylphenyl iodonium) acetate

Product 1

HCID 131728419Bis (4-t-butylphenyl iodonium) triphenyl sulfonium perfluorobutane-1,4-disulfonate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

4.73 g of triphenyl sulfonium bromide was dissolved in water in a flask. Bis (4-t-butylphenyl iodonium) acetate (6.24 g) was dissolved in acetone and added to the flask. Perfluorobutane-1,4-disulfonic acid (5.0 g) was then added to the mixture and the mixture was stirred over night at room temperature. Bis (4-t-butylphenyl iodonium) triphenyl sulfonium perfluorobutane-1,4-disulfonate was isolated as in Example 1 (mixture of compounds); mp 93° C.

Workup

  1. additionadded to the flask

Sources & evidence

ORD record
ord-be4c57ae49ed44e29ea4157d11fc05d0
Source dataset
uspto-grants-2010_11
Patent number
US07833693B2

Reaction notes

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