Methyl p-toluenesulfonate → Bis(4-tert-butylphenyl)iodonium p-toluenesulfonate

HRID 2057135Notes

Reaction equation

HRID 2057135 reaction equation
C([O-])(=O)C.[C:5]([C:9]1[CH:14]=[CH:13][C:12]([I+:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:18][CH:17]=2)=[CH:11][CH:10]=1)([CH3:8])([CH3:7])[CH3:6].[C:26]1([CH3:37])[CH:31]=[CH:30][C:29]([S:32]([O:35]C)(=[O:34])=[O:33])=[CH:28][CH:27]=1>COC(C)(C)C>[C:26]1([CH3:37])[CH:27]=[CH:28][C:29]([S:32]([O-:35])(=[O:33])=[O:34])=[CH:30][CH:31]=1.[C:22]([C:19]1[CH:20]=[CH:21][C:16]([I+:15][C:12]2[CH:11]=[CH:10][C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])=[CH:14][CH:13]=2)=[CH:17][CH:18]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 21909498Iodonium, bis[4-(1,1-dimethylethyl)phenyl]-, acetate

Product 1

HCID 16216932Bis(4-tert-butylphenyl)iodonium p-toluenesulfonateYield 92.3%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

Bis(p-tert-butylphenyl)iodonium acetate (467 mg; 1.0 mmol) and methyl p-toluenesulfonate (204 mg; 1.1 mmol) were suspended in t-butyl methyl ether (5 ml). The suspension was heated at 55° C.-58° C. and refluxed for 5 hours while being stirred. The reaction mixture was cooled, and formed white solid was removed through filtration. The white solid was washed with t-butyl methyl ether, and dried under vacuum, to thereby yield 521 mg of bis(p-tert-butylphenyl)iodonium p-toluenesulfonate (yield: 91%).

Workup

  1. temperatureThe suspension was heated at 55° C.-58° C.
  2. temperaturerefluxed for 5 hours
  3. temperatureThe reaction mixture was cooled
  4. customformed white solid
  5. customwas removed through filtration
  6. washThe white solid was washed with t-butyl methyl ether
  7. customdried under vacuum

Sources & evidence

ORD record
ord-bab00b99c87a4235bfe1c65b95a4d765
Source dataset
uspto-grants-2008_02
Patent number
US07335787B2

Reaction notes

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