Tetrafluoroboric acid → Diphenyliodonium Tetrafluoroborate

HRID 341872

Reaction equation

HRID 341872 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.[F:19][B-:20]([F:23])([F:22])[F:21].[H+].P(O)(O)O.[Cl-].C1([I+]C2C=CC=CC=2)C=CC=CC=1>O.F[B-](F)(F)F.[Ag+]>[F:19][B-:20]([F:23])([F:22])[F:21].[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

7

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 73870Diphenyliodonium chlorideHCID 107909Phosphorous acidHCID 170803Iodonium, diphenyl-, sulfate (1:1)

Product 1

HCID 11122160Diphenyliodonium Tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 962WaterSolvent

Procedure

The aromatic iodonium complex salts may be prepared by metathesis of corresponding aromatic iodonium simple salts (such as, for example, the diphenyliodonium bisulfate) in accordance with the teachings of Beringer, et al., J. Am. Chem. Soc 81,342 (1959). Thus, for examples, the complex salt diphenyliodonium tetrafluoroborate is prepared by the addition at 60° C. of an aqueous solution containing 29.2 g (150 millimoles) silver fluoroborate, 2 g. fluoroboric acid, and 0.5 g phosphorous acid in about 30 ml of water to a solution of 44 g (139 millimoles) of diphenyliodonium chloride. The silver halide that precipitates is filtered off and the filtrate concentrated to yield diphenyliodonium fluoroborate which may be purified by recrystallization.

Workup

  1. customis prepared by the addition at 60° C. of an aqueous solution
  2. customThe silver halide that precipitates
  3. filtrationis filtered off
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-44f9ce577dfd4dff9a2a2ba86cf430a4
Source dataset
uspto-grants-1999_01
Patent number
US05856373

Linked notes

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