Iodonium, bis[4-(1,1-dimethylethyl)phenyl]-, chloride → Bis(p-tert-butylphenyl)iodonium 9,10-dimethoxyanthracene-2-sulfonate

HRID 1168009Notes

Reaction equation

HRID 1168009 reaction equation
[Cl-].[C:2]([C:6]1[CH:11]=[CH:10][C:9]([I+:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)([CH3:5])([CH3:4])[CH3:3].[CH3:23][O:24][C:25]1[C:26]2[C:31]([C:32]([O:44][CH3:45])=[C:33]3[C:38]=1[CH:37]=[C:36]([S:39]([O:42]C)(=[O:41])=[O:40])[CH:35]=[CH:34]3)=[CH:30][CH:29]=[CH:28][CH:27]=2>C(#N)C>[CH3:23][O:24][C:25]1[C:26]2[C:31]([C:32]([O:44][CH3:45])=[C:33]3[C:38]=1[CH:37]=[C:36]([S:39]([O-:42])(=[O:40])=[O:41])[CH:35]=[CH:34]3)=[CH:30][CH:29]=[CH:28][CH:27]=2.[C:19]([C:16]1[CH:17]=[CH:18][C:13]([I+:12][C:9]2[CH:8]=[CH:7][C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])=[CH:11][CH:10]=2)=[CH:14][CH:15]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 21889439Iodonium, bis[4-(1,1-dimethylethyl)phenyl]-, chlorideHCID 22995013Methyl 9,10-dimethoxyanthracene-2-sulfonate

Product 1

HCID 22995016Bis(p-tert-butylphenyl)iodonium 9,10-dimethoxyanthracene-2-sulfonateYield 78%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Acetonitrile (90 ml) was added to bis(p-tert-butylphenyl)iodonium chloride (6.4 g; 15 mmol) and methyl 9,10-dimethoxyanthracene-2-sulfonate (6.48 g; 19.5 mmol). The resultant mixture was heated at 82° C.-85° C. and refluxed for 20 hours while being stirred. The reaction mixture was cooled, and precipitated solid was separated through filtration. The solid was washed with ethyl acetate, and dried under vacuum, to thereby yield 8.32 g of bis(p-tert-butylphenyl)iodonium 9,10-dimethoxyanthracene-2-sulfonate (yield: 78%). The chloride anion content of the resultant solid was 110 ppm, as determined by silver nitrate titration.

Workup

  1. temperaturerefluxed for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. customprecipitated solid
  4. customwas separated through filtration
  5. washThe solid was washed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-ec9314f1770e4db9adb65ab246b6c79c
Source dataset
uspto-grants-2003_09
Patent number
US06620957B1

Reaction notes

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