Iodonium, diphenyl-, sulfate (1:1) → Diphenyliodonium phenylsulfate

HRID 585029Notes

Reaction equation

HRID 585029 reaction equation
S([O-])(O)(=O)=O.[C:6]1([I+:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:19]1([O:25][S:26]([O-:29])(=[O:28])=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[N+](C)(C)C>O>[C:19]1([O:25][S:26]([O-:29])(=[O:28])=[O:27])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1.[C:13]1([I+:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 170803Iodonium, diphenyl-, sulfate (1:1)HCID 22338997Tetramethylammonium phenylsulfate

Product 1

HCID 22339003Diphenyliodonium phenylsulfateYield 35.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

3 g of the crude diphenyliodonium hydrogensulfate are dissolved in 50 ml of water. To the solution is added a solution of 2.35 g of the crude tetramethylammonium phenylsulfate dissolved in 10 ml of water. The mixture is stirred for 7 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 recrystallization from 1,2-dichloroethane, yielding 1.29 g of diphenyliodonium phenylsulfate as a white solid, mp. 129-132° C. The structure is confirmed by the 1H-NMR spectrum (CDCl6/DMSO-d6). δ [ppm]: 7.08 (t, 1H), 7.22-7.30 (m, 4H), 7.42 (t, 4H), 7.58 (t, 2H), 7.92 (d, 4H).

Workup

  1. extractionThe product is extracted with methylene chloride
  2. washthe organic layer is washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by recrystallization from 1,2-dichloroethane

Sources & evidence

ORD record
ord-c0ed69020b804349b26ed13375f5a056
Source dataset
uspto-grants-2005_08
Patent number
US06929896B2

Reaction notes

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