Potassium Carbonate → Biphenyl

HRID 918938Notes

Reaction equation

HRID 918938 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]1(OB(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+]>O.C(O)C>[C:2]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 7095BiphenylYield 90%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
60 °C

Procedure

After obtaining the supported metal nanoparticles, the catalytic activity was examined using a very popular cross coupling reaction—Suzuki reaction, which is commonly used in the pharmaceutical industry, as shown in FIG. 8. Still referring to FIG. 8, Iodobenzene (0.5 mmol), phenyl boric acid (0.8 mmol) and K2CO3 (1.0 mmol) were added to a 4 mL mixture of a water:ethanol (1:1) solution. Then, the supported nano-Pd on XAD-4 (100 mg) was added, and the reaction mixture was heated to 60° C. for 12 hours. The supported catalyst was recovered by filtration, and the filtrate was extracted by ether. The evaporation of ether furnished the crude product, which was purified by regular flash column chromatography, as known to those of ordinary skill in the art, to yield pure biphenyl in 90% yield. The supported metal nanoparticles could be reused three times without significant activity loss.

Workup

  1. customAfter obtaining the supported metal nanoparticles
  2. customa very popular cross coupling reaction—Suzuki reaction, which
  3. filtrationThe supported catalyst was recovered by filtration
  4. extractionthe filtrate was extracted by ether
  5. customThe evaporation of ether
  6. customfurnished the crude product, which
  7. customwas purified by regular flash column chromatography

Sources & evidence

ORD record
ord-7dfc839cf1574568a6486039e9d49db9
Source dataset
uspto-grants-2016_03
Patent number
US09272260B2

Reaction notes

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