Potassium Carbonate → (3-Phenylphenyl)boronic acid

HRID 1179095Notes

Reaction equation

HRID 1179095 reaction equation
[C:1]1([B:7]([OH:9])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(COC)OC>[C:3]1([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=[CH:5][CH:6]=[C:1]([B:7]([OH:9])[OH:8])[CH:2]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 66827Phenylboronic AcidHCID 2734318(3-Bromophenyl)boronic acid

Product 1

HCID 2734315(3-Phenylphenyl)boronic acidYield 87%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Phenyl boronic acid (1) (106.2 g, 871.4 mmol), 3-bromophenylboronic acid (2) (35.0 g, 174.2 mmol), palladium acetate (9.8 g, 4.357 mmol), triphenylphosphine (4.64 g, 17.4 mmol), and 2M K2CO3 aqueous solution (470 ml) were added to 950 mL of dimethoxyethane and refluxed for 17 hours. The mixture was cooled to room temperature and the aqueous layer was separated from the organic layer. The aqueous layer was then extracted twice with 200 mL of ethyl acetate. The organic layers were combined and washed with brine and dried over magnesium sulfate. The solids were removed by vacuum filtration and the organic solvent evaporated to the crude product. The crude product was purified by Kugelehor distillation to give of 3 (30 g, 86.7%).

Workup

  1. temperaturerefluxed for 17 hours
  2. customthe aqueous layer was separated from the organic layer
  3. extractionThe aqueous layer was then extracted twice with 200 mL of ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solids were removed by vacuum filtration
  7. customthe organic solvent evaporated to the crude product
  8. distillationThe crude product was purified by Kugelehor distillation

Sources & evidence

ORD record
ord-1ee2d78665db4b76a635dd67baf81b7c
Source dataset
uspto-grants-2007_10
Patent number
US07279232B2

Reaction notes

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