Reaction #1797496

ord-fe457116d48a4bb1b83986cd95c506f1

Reaction equation

F[P-](F)(F)(F)(F)F.c1ccc([I+]c2ccccc2)cc1
diphenyliodonium hexafluorophosphate
F[B-](F)(F)F.[H+]
fluoroboric acid
OP(O)O
phosphorous acid
[Cl-].c1ccc([I+]c2ccccc2)cc1
diphenyliodonium chloride
F[B-](F)(F)F.c1ccc([I+]c2ccccc2)cc1
diphenyliodonium fluoroborate

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otheris prepared by the addition at 60° C. of an aqueous solution
  2. 2
    OtherThe silver halide that precipitates
  3. 3
    Filtrationis filtered off
  4. 4
    Concentrationthe filtrate concentrated

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 is 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 precipitates is filtered off and the filtrate concentrated to yield diphenyliodonium fluoroborate which may be purified by recrystallization.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07790353B2uspto-grants-2010_09