Dichloromethane → (4-Methylphenyl)(4'-isobutylphenyl)iodonium phenylsulfate

HRID 585033Notes

Reaction equation

HRID 585033 reaction equation
[C:1]1([O:7][S:8]([O-:11])(=[O:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+](C)(C)C.S([O-])(O)(=O)=O.[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([I+:29][C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH:37]([CH3:39])[CH3:38])=[CH:32][CH:31]=2)=[CH:25][CH:24]=1.C(Cl)Cl>O.CO>[C:1]1([O:7][S:8]([O-:11])(=[O:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:22][C:23]1[CH:24]=[CH:25][C:26]([I+:29][C:30]2[CH:35]=[CH:34][C:33]([CH2:36][CH:37]([CH3:39])[CH3:38])=[CH:32][CH:31]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22338997Tetramethylammonium phenylsulfateHCID 86591397(4-Methylphenyl)(4'-isobutylphenyl)iodonium hydrogensulfate

Product 1

HCID 22339001(4-Methylphenyl)(4'-isobutylphenyl)iodonium phenylsulfateYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

0.98 g of the crude tetramethylammonium phenylsulfate, prepared according to the method of Example 1.2, are dissolved in 10 ml of water. 1.48 g of the crude (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate, dissolved in 10 ml of methanol, are added to the solution. The mixture is stirred for 1 hour at room temperature. 10 ml of methylene chloride are added to the solution and stirred for additional 3 hours at room temperature. The product is extracted with methylene chloride and the organic layer is washed with water, dried over MgSO4, and concentrated. The residue is purified by flash chromatography on silica gel with methylene chloride, followed by methylene chloride and ethanol (95:5) as an eluent, yielding 1.54 g of (4-methylphenyl)(4′-isobutylphenyl)iodonium phenylsulfate as a pale yellow resin. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.87 (d, 6H), 1.78-1.87 (m, 11H), 2.37 (s, 3H), 2.47 (d, 2H), 7.08 (t, 1H), 7.13-7.31 (m, 8H), 7.77 (d, 4H).

Workup

  1. additionare added to the solution
  2. stirringstirred for additional 3 hours at room temperature
  3. extractionThe product is extracted with methylene chloride
  4. washthe organic layer is washed with water
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography on silica gel with methylene chloride

Sources & evidence

ORD record
ord-9bfcbe76c59b48f281f286552ee4d512
Source dataset
uspto-grants-2005_08
Patent number
US06929896B2

Reaction notes

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