Water → Bis(pentafluorophenyl)borinic acid

HRID 2414468Notes

Reaction equation

HRID 2414468 reaction equation
S([O-])([O-])(=O)=O.[Al+3].S([O-])([O-])(=O)=O.S([O-])([O-])(=O)=O.[Al+3].[OH2:18].[F:19][C:20]1[C:25]([B:26](C2C(F)=C(F)C(F)=C(F)C=2F)[C:27]2[C:32]([F:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=2[F:37])=[C:24]([F:49])[C:23]([F:50])=[C:22]([F:51])[C:21]=1[F:52]>C1(C)C=CC=CC=1>[F:19][C:20]1[C:25]([B:26]([C:27]2[C:32]([F:33])=[C:31]([F:34])[C:30]([F:35])=[C:29]([F:36])[C:28]=2[F:37])[OH:18])=[C:24]([F:49])[C:23]([F:50])=[C:22]([F:51])[C:21]=1[F:52]

Participants

5

Reactant 3

HCID 962WaterHCID 24850Aluminum Sulfate2×HCID 582056Tris(pentafluorophenyl)borane2×

Product 1

HCID 9841889Bis(pentafluorophenyl)borinic acid

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Moreover, that patent also discloses a method in which aluminum sulfate 18 hydrate is used instead of water. Specifically, aluminum sulfate 18 hydrate containing water of 1.77 molar equivalent vs. tris(pentafluorophenyl)borane is added to a toluene solution of tris(pentafluorophenyl)borane. After the solution is refluxed, insoluble aluminum sulfate is separated from the reaction mixture. A solvent of the filtrate is removed in vacuo. Toluene is added to the thus obtained residues. After stirring, the insoluble material is filtered through a G4 sintered-glass so as to be separated. The solvent of the filtrate is again removed in vacuo. Heptane is added to the residues. The solution is stirred and filtered so that a cake is obtained. Finally, the thus obtained cake is washed with heptane, and dried in vacuo so as to isolate bis(pentafluorophenyl)borinic acid. However, this method has such a problem that it is necessary to remove the byproduct aluminum sulfate and its process is so complicated.

Workup

  1. temperatureAfter the solution is refluxed
  2. custominsoluble aluminum sulfate is separated from the reaction mixture
  3. customA solvent of the filtrate is removed in vacuo
  4. additionToluene is added to the thus obtained residues
  5. filtrationthe insoluble material is filtered through a G4 sintered-glass so as
  6. customto be separated
  7. customThe solvent of the filtrate is again removed in vacuo
  8. additionHeptane is added to the residues
  9. stirringThe solution is stirred
  10. filtrationfiltered so that a cake
  11. customis obtained
  12. washFinally, the thus obtained cake is washed with heptane
  13. customdried in vacuo so as

Sources & evidence

ORD record
ord-cf106301db9a4b18a2e158ee1f2c22c0
Source dataset
uspto-grants-2004_11
Patent number
US06812360B2

Reaction notes

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