Methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate → Bis(p-tert-butylphenyl)iodonium camphorsulfonate

HRID 1168013Notes

Reaction equation

HRID 1168013 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]12([CH2:36][S:37]([O:40]C)(=[O:39])=[O:38])[C:33]([CH3:35])([CH3:34])[CH:30]([CH2:31][CH2:32]1)[CH2:29][C:27]2=[O:28]>C(OCC)(=O)C>[C:26]12([CH2:36][S:37]([O-:40])(=[O:38])=[O:39])[C:33]([CH3:35])([CH3:34])[CH:30]([CH2:31][CH2:32]1)[CH2:29][C:27]2=[O:28].[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 573022Methyl (7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonateHCID 21909498Iodonium, bis[4-(1,1-dimethylethyl)phenyl]-, acetate

Product 1

HCID 21930728Bis(p-tert-butylphenyl)iodonium camphorsulfonateYield 83%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Ethyl acetate (50 ml) was added to bis(p-tert-butylphenyl)iodonium acetate (467 mg; 1 mmol) and methyl camphorsulfonate (259 mg; 1.05 mmol). The resultant mixture was refluxed for 24 hours while being stirred. The reaction mixture was cooled, and formed solid was removed through filtration. The solid was recrystallized from acetone, and dried under vacuum, to thereby yield 518 mg of bis(p-tert-butylphenyl)iodonium camphorsulfonate (yield: 83%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customformed solid
  3. customwas removed through filtration
  4. customThe solid was recrystallized from acetone
  5. customdried under vacuum

Sources & evidence

ORD record
ord-38c340f477e14924a15db84190af7c68
Source dataset
uspto-grants-2003_09
Patent number
US06620957B1

Reaction notes

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