Tetrafluoroboric acid → Diphenyliodonium Tetrafluoroborate

HRID 1374507Notes

Reaction equation

HRID 1374507 reaction equation
F[P-](F)(F)(F)(F)F.[C:8]1([I+:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[F:21][B-:22]([F:25])([F:24])[F:23].[H+].P(O)(O)O.[Cl-].C1([I+]C2C=CC=CC=2)C=CC=CC=1>O.F[B-](F)(F)F.[Ag+]>[F:21][B-:22]([F:25])([F:24])[F:23].[C:15]1([I+:14][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 28118Tetrafluoroboric acidHCID 73870Diphenyliodonium chlorideHCID 107909Phosphorous acidHCID 2737136Iodonium, diphenyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 11122160Diphenyliodonium Tetrafluoroborate

Reagents, catalysts & solvents 2

HCID 159722Silver tetrafluoroborateCatalystHCID 962WaterSolvent

Procedure

The aromatic iodonium complex salts such as diphenyliodonium hexafluorophosphate 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 was prepared by the addition at 60° C. of an aqueous solution containing 29.2 grams (g) silver fluoroborate, 2 g fluoroboric acid, and 0.5 g phosphorous acid in about 30 milliliters (mL) of water to a solution of 44 g (139 millimoles) of diphenyliodonium chloride. The silver halide that precipitated was filtered off and the filtrate concentrated to yield diphenyliodonium fluoroborate, which may be purified by recrystallization.

Workup

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

Sources & evidence

ORD record
ord-326d390332b54d6abe7cfff885ba1343
Source dataset
uspto-grants-2007_01
Patent number
US07166409B2

Reaction notes

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