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

HRID 2179875Notes

Reaction equation

HRID 2179875 reaction equation
S([O-])([O-])(=O)=O.[C:6]([C:11]1[CH:16]=[CH:15][C:14]([IH+:17])=[CH:13][CH:12]=1)([CH2:9][CH3:10])([CH3:8])[CH3:7].[C:18]([C:23]1[CH:28]=[CH:27][C:26]([IH+])=[CH:25][CH:24]=1)([CH2:21][CH3:22])([CH3:20])[CH3:19].[F:30][C:31]1[C:36]([S:37]([O-:40])(=[O:39])=[O:38])=[C:35]([F:41])[C:34]([F:42])=[C:33]([F:43])[C:32]=1[F:44].C[N+](C)(C)C>O>[F:30][C:31]1[C:36]([S:37]([O-:40])(=[O:39])=[O:38])=[C:35]([F:41])[C:34]([F:42])=[C:33]([F:43])[C:32]=1[F:44].[C:6]([C:11]1[CH:12]=[CH:13][C:14]([I+:17][C:26]2[CH:25]=[CH:24][C:23]([C:18]([CH2:21][CH3:22])([CH3:19])[CH3:20])=[CH:28][CH:27]=2)=[CH:15][CH:16]=1)([CH2:9][CH3:10])([CH3:7])[CH3:8]

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

60 g of t-amylbenzene, 39.5 g of potassium iodate, 81 g of acetic anhydride and 170 ml of dichloromethane were mixed together. Then 66.8 g of conc. sulfuric acid was slowly added dropwise thereinto under ice-cooling. After stirring under ice-cooling for 2 hours, the mixture was stirred at room temperature for additional 10 hours. 500 ml of water was added to the liquid reaction mixture under ice-cooling and the mixture was extracted with dichloromethane. The organic phase was washed with sodium hydrogencarbonate and water and then concentrated to give (4-t-amylphenyl)iodonium sulfate. This sulfate was added to a solution of tetramethylammonium pentafluorobenzenesulfonate in excess. After adding 500 ml of water, 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 give di(4-t-amylphenyl)iodonium pentafluorobenzenesulfonate (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-806f0db4e285436185823604d705889d
Source dataset
uspto-grants-2005_05
Patent number
US06887645B2

Reaction notes

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