Water → Biphenyl

HRID 241316Notes

Reaction equation

HRID 241316 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[C:16]1(B(O)O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C(O)(C)C>[C:2]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7961Bromobenzene2×HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic Acid

Product 1

HCID 7095BiphenylYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

(28 mmol, 1 eq.) of bromobenzene and 9 g (42 mmol, 1.5 eq.) of K3PO4 are added to a solution of 5.13 g (42 mmol, 1.5 eq.) of phenylboronic acid in 60 ml of isopropanol. The mixture is stirred at room temperature for 45 minutes, and 0.02 g (14.03 μmol, 0.05 mol %) of [{Pd[P(C2F5)2O]2H}2(μ-Cl)2], prepared in accordance with Example 13, is subsequently added, and the reaction mixture is stirred at room temperature for 3 hours. After addition of 100 ml of water, the reaction mixture is extracted with 200 ml of hexane. The organic phase is washed with saturated sodium chloride solution and dried using MgSO4. After filtration and removal of the solvent (in vacuo), 3.16 g of biphenyl are isolated as a white solid. The yield is 73%, based on the amount of bromobenzene employed.

Workup

  1. additionis subsequently added
  2. stirringthe reaction mixture is stirred at room temperature for 3 hours
  3. extractionthe reaction mixture is extracted with 200 ml of hexane
  4. washThe organic phase is washed with saturated sodium chloride solution
  5. customdried
  6. filtrationAfter filtration and removal of the solvent (in vacuo), 3.16 g of biphenyl
  7. customare isolated as a white solid

Sources & evidence

ORD record
ord-f2dfc73dcad147a18d1f688b004a65fc
Source dataset
uspto-grants-2014_02
Patent number
US08648202B2

Reaction notes

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