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

HRID 585034Notes

Reaction equation

HRID 585034 reaction equation
[C:1]1([CH2:7][O:8][S:9]([O-:12])(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N+](C)(C)C.S([O-])(O)(=O)=O.[CH3:23][C:24]1[CH:29]=[CH:28][C:27]([I+:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH:38]([CH3:40])[CH3:39])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1.C(Cl)Cl>O.CO>[C:1]1([CH2:7][O:8][S:9]([O-:12])(=[O:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:23][C:24]1[CH:25]=[CH:26][C:27]([I+:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][CH:38]([CH3:40])[CH3:39])=[CH:33][CH:32]=2)=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22339010Tetramethylammonium phenylmethylsulfateHCID 86591397(4-Methylphenyl)(4'-isobutylphenyl)iodonium hydrogensulfate

Product 1

HCID 22338999(4-Methylphenyl)(4'-isobutylphenyl)iodonium phenylmethylsulfateYield 73.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

1.03 g of the crude tetramethylammonium phenylmethylsulfate are dissolved in 10 ml of water. 1.48 g of the crude (4-methylphenyl)(4′-isobutylphenyl)iodonium hydrogensulfate (obtained according to example 7.1), 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 additonal 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 1.31 g of (4-methylphenyl)(4′-isobutylphenyl)iodonium phenylmethylsulfate as a pale brown resin. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.86 (d, 6H), 1.80-1.85 (m, 1H), 2.36 (s, 3H), 2.45 (d, 2H), 4.97 (s, 2H), 7.12-7.37 (m, 9H), 7.77-7.81 (m, 4H).

Workup

  1. additionare added to the solution
  2. stirringstirred for additonal 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-bcf46c2bb70749d487bd228eca15257d
Source dataset
uspto-grants-2005_08
Patent number
US06929896B2

Reaction notes

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