Phenylboronic Acid → Diphenyliodonium Tetrafluoroborate

HRID 1500207Notes

Reaction equation

HRID 1500207 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[C:14]1[C:15](OC(=O)C)=[C:16]([I:20])[CH:17]=[CH:18][CH:19]=1)(=O)C.[F:25][B-:26]([F:29])([F:28])[F:27].[Na+]>C(Cl)Cl>[F:25][B-:26]([F:29])([F:28])[F:27].[C:1]1([I+:20][C:16]2[CH:17]=[CH:18][CH:19]=[CH:14][CH:15]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 4343483Sodium TetrafluoroborateHCID 21865429Bis(acetoxy)iodobenzene

Product 1

HCID 11122160Diphenyliodonium TetrafluoroborateYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Phenylboronic acid (0.79 g, 6.5 mmol), methylene chloride (62 ml), and boron trifluoride ethyl ether complex (0.97 g, 6.8 mmol) were charged and cooled to 0° C. A solution of diacetoxy iodobenzene (2.0 g, 6.2 mmol) in methylene chloride (62 ml) was added dropwise. The reaction was carried out at 0° C. for 1.5 hours. A saturated aqueous solution of sodium fluoroborate (13.6 g, 124.2 mmol) was added dropwise, and the mixture was extracted with addition of water and methylene chloride. The organic layer was dried with anhydrous sodium sulfate, concentrated to dryness under reduced pressure, and purified by recrystallization to give the title compound (2.13 g, 93.5%).

Workup

  1. extractionthe mixture was extracted with addition of water and methylene chloride
  2. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  3. concentrationconcentrated to dryness under reduced pressure
  4. custompurified by recrystallization

Sources & evidence

ORD record
ord-7ec935c627814859b74ae8934ca6bb93
Source dataset
uspto-grants-2015_12
Patent number
US09206129B2

Reaction notes

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