Tetramethylammonium pentafluorobenzenesulfonate → Di(4-t-amylphenyl)iodonium pentafluorobenzenesulfonate

HRID 1635787Notes

Reaction equation

HRID 1635787 reaction equation
[F:1][C:2]1[C:7]([S:8]([O-:11])(=[O:10])=[O:9])=[C:6]([F:12])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[F:15].C[N+](C)(C)C.S([O-])([O-])(=O)=O.[C:26]([C:31]1[CH:36]=[CH:35][C:34]([IH+:37])=[CH:33][CH:32]=1)([CH2:29][CH3:30])([CH3:28])[CH3:27].[C:38]([C:43]1[CH:48]=[CH:47][C:46]([IH+])=[CH:45][CH:44]=1)([CH2:41][CH3:42])([CH3:40])[CH3:39]>O>[F:1][C:2]1[C:7]([S:8]([O-:11])(=[O:10])=[O:9])=[C:6]([F:12])[C:5]([F:13])=[C:4]([F:14])[C:3]=1[F:15].[C:26]([C:31]1[CH:32]=[CH:33][C:34]([I+:37][C:46]2[CH:45]=[CH:44][C:43]([C:38]([CH2:41][CH3:42])([CH3:39])[CH3:40])=[CH:48][CH:47]=2)=[CH:35][CH:36]=1)([CH2:29][CH3:30])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 21964803Tetramethylammonium pentafluorobenzenesulfonateHCID 865852084-t-Amylphenyliodonium sulfate

Product 1

HCID 22486725Di(4-t-amylphenyl)iodonium pentafluorobenzenesulfonate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

t-Amylbenzene (60 g), 39.5 g of potassium iodate, 81 g of acetic anhydride and 170 ml of dichloromethane were mixed, and 66.8 g of concentrated sulfuric acid was slowly added dropwise thereto under ice cooling. After stirring for 2 hours under ice cooling, the mixture was stirred at room temperature for 10 hours. Then, 500 ml of water was added to the reaction solution under ice cooling, and the resulting solution was extracted with dichloromethane. The organic phase was washed with sodium hydrogen carbonate and water, and then concentrated to obtain di (4-t-amylphenyliodonium sulfate. To a solution of tetramethylammonium pentafluorobenzenesulfonate in excess the obtained sulfate was added. Then, 500 ml of water was added to the solution, and the solution was extracted with dichloromethane. Then, the organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water, and then concentrated to obtain di(4-t-amylphenyl)iodonium penta-fluorobenzenesulfonate (III-1).

Workup

  1. extractionthe solution was extracted with dichloromethane
  2. washThen, the organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cd2ce376a95d45cbb3d294d991b8eca5
Source dataset
uspto-grants-2003_01
Patent number
US06511783B1

Reaction notes

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