Tetramethylammonium pentafluorobenzenesulfonate → HCID 86759414, compound

HRID 2085004Notes

Reaction equation

HRID 2085004 reaction equation
S([O-])([O-])(=O)=O.C([C:11]1[CH:16]=[CH:15][C:14]([I+:17][C:18]2[CH:23]=[CH:22][C:21](C(CC)(C)C)=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)(CC)(C)C.[C:29]([C:34]1C=CC([I+]C2C=CC(C(CC)(C)C)=CC=2)=C[CH:35]=1)([CH2:32][CH3:33])(C)C.[F:52][C:53]1[C:58]([S:59]([O-:62])(=[O:61])=[O:60])=[C:57]([F:63])[C:56]([F:64])=[C:55]([F:65])[C:54]=1[F:66].C[N+](C)(C)C>O>[F:52][C:53]1[C:58]([S:59]([O-:62])(=[O:61])=[O:60])=[C:57]([F:63])[C:56]([F:64])=[C:55]([F:65])[C:54]=1[F:66].[CH2:33]([C:11]1[CH:16]=[CH:15][C:14]([I+:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:55][CH2:54][CH2:53][CH2:58][CH3:57])=[CH:20][CH:19]=2)=[CH:13][CH:12]=1)[CH2:32][CH2:29][CH2:34][CH3:35]

Participants

4

Reactant 2

HCID 21964803Tetramethylammonium pentafluorobenzenesulfonateHCID 71350713Bis{bis[4-(2-methylbutan-2-yl)phenyl]iodanium} sulfate

Product 1

HCID 86759414HCID 86759414, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under ice-cooling, 25 g of pentafluorobenzenesulfonyl and 66.8 g of concentrated sulfuric acid was gradually dropwise added to the mixture with ice-cooling. The mixture was stirred with ice-cooling for 2 hours and then at room temperature for 10 hours. With ice-cooling, 500 ml of water was added to the reaction solution, followed by extraction with dichloromethane. The organic phase was washed with sodium bicarbonate and water and then concentrated, thereby a di (4-t-amylphenyl) iodonium sulfate was obtained. The sulfate was added to a solution containing an excess amount of tetramethylammonium pentafluorobenzenesulfonate. Water (500 ml) was added to the solution, followed by extraction with dichloromethane. The organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water, and then concentrated, thereby di (4-amylphenyl) iodonium pentafluorobenzenesulfonate was obtained.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic phase was washed with a 5% aqueous solution of tetramethylammonium hydroxide and water
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cbffeaf887d84aa2b8069ab2cfffd46d
Source dataset
uspto-grants-2004_04
Patent number
US06720128B2

Reaction notes

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