Tetrafluoroboric acid → Diphenyliodonium Tetrafluoroborate

HRID 481145Notes

Reaction equation

HRID 481145 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[H+].P(O)(O)O.[Cl-].[C:12]1([I+:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>O.F[B-](F)(F)F.[Ag+]>[F:1][B-:2]([F:5])([F:4])[F:3].[C:19]1([I+:18][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 73870Diphenyliodonium chlorideHCID 107909Phosphorous acid

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, diphenyliodonium bisulfate) in accordance with the teachings of Beringer et al., J. Am. Chem. Soc., 81,342 (1959). Thus, for example, the complex salt diphenyliodonium tetrafluoroborate is prepared by the addition at 60° C. of an aqueous solution containing 29.2 g 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-675f36f9fc354784b4b54dca52c9e683
Source dataset
uspto-grants-2003_11
Patent number
US06653486B2

Reaction notes

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