Tetrafluoroboric acid → Diphenyliodonium Tetrafluoroborate

HRID 372354Notes

Reaction equation

HRID 372354 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>F[B-](F)(F)F.[Ag+].O>[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 gy 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. additionthe addition at 60° C. of an aqueous solution
  2. additioncontaining 29.2 g
  3. customThe silver halide that precipitates
  4. filtrationis filtered off
  5. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-f2a48067779641f884f088d03abc6070
Source dataset
uspto-grants-1978_05
Patent number
US04090936

Reaction notes

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