Water → Biphenyl

HRID 241315Notes

Reaction equation

HRID 241315 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:14]1(B(O)O)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>O1CCCC1>[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 66827Phenylboronic Acid

Product 1

HCID 7095BiphenylYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.57 g (10 mmol) of bromobenzene and 4.15 g (30 mmol) of K2CO3 are added to a solution of 1.83 g (15 mmol) of phenylboronic acid in 20 ml of tetrahydrofuran. After the mixture has been stirred at room temperature for 15 minutes, 0.21 g (0.15 mmol) of [{Pd[P(C2F5)2O]2H}2(μ-Cl)2], prepared in accordance with Example 13, is added, and the reaction mixture is heated under reflux for 3 hours. After cooling and addition of 100 ml of water, the reaction mixture is extracted with 200 ml of hexane. The organic phase is washed with water and dried using MgSO4. After filtration and removal of the solvent (in vacuo), 0.99 g of biphenyl is isolated as a white solid. The yield is 64%, based on the bromobenzene employed.

Workup

  1. additionis added
  2. temperaturethe reaction mixture is heated
  3. temperatureunder reflux for 3 hours
  4. temperatureAfter cooling
  5. extractionthe reaction mixture is extracted with 200 ml of hexane
  6. washThe organic phase is washed with water
  7. customdried
  8. filtrationAfter filtration and removal of the solvent (in vacuo)

Sources & evidence

ORD record
ord-52816a4bdbed4136a3ba4c39e0a17c14
Source dataset
uspto-grants-2014_02
Patent number
US08648202B2

Reaction notes

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