Dichloromethane → Di(4-tert-amylphenyl)iodonium propylsulfate

HRID 585031Notes

Reaction equation

HRID 585031 reaction equation
[CH2:1]([O:4][S:5]([O-:8])(=[O:7])=[O:6])[CH2:2][CH3:3].C[N+](C)(C)C.S([O-])(O)(=O)=O.[C:19]([C:24]1[CH:29]=[CH:28][C:27]([I+:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([CH2:40][CH3:41])([CH3:39])[CH3:38])=[CH:33][CH:32]=2)=[CH:26][CH:25]=1)([CH2:22][CH3:23])([CH3:21])[CH3:20].C(Cl)Cl>O.CO>[CH2:1]([O:4][S:5]([O-:8])(=[O:7])=[O:6])[CH2:2][CH3:3].[C:37]([C:34]1[CH:35]=[CH:36][C:31]([I+:30][C:27]2[CH:28]=[CH:29][C:24]([C:19]([CH2:22][CH3:23])([CH3:21])[CH3:20])=[CH:25][CH:26]=2)=[CH:32][CH:33]=1)([CH2:40][CH3:41])([CH3:39])[CH3:38]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 22338987Tetramethylammonium propylsulfateHCID 71357610Bis[4-(2-methylbutan-2-yl)phenyl]iodanium hydrogen sulfate

Product 1

HCID 22338996Di(4-tert-amylphenyl)iodonium propylsulfateYield 52.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

3.4 g of the crude tetramethylammonium propylsulfate are dissolved in 10 ml of water. To the solution are added 6.8 g of the crude di(4-tert-amylphenyl)iodonium hydrogensulfate prepared according to the method of example 3.1, dissolved in 5 ml of methanol. The mixture is stirred for 4 hours at room temperature. 10 ml of methylene chloride are added to the solution and stirred for additonal 2 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 3.86 g of di(4-tert-amylphenyl)iodonium propylsulfate as a brownish solid, mp. 48-53° C. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 0.65 (t, 6H), 0.88 (t, 3H), 1.24 (s, 12H), 1.56-1.66 (m, 6H), 3.89 (t, 2H), 7.37 (d, 4H), 7.88 (d, 4H).

Workup

  1. customprepared
  2. stirringstirred for additonal 2 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-27b05290c8414f279d8a0e16a4c8cc7e
Source dataset
uspto-grants-2005_08
Patent number
US06929896B2

Reaction notes

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