4-Bromotoluene → 4-Methylbiphenyl

HRID 1686370Notes

Reaction equation

HRID 1686370 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9]1(B(O)O)[CH:14]=[CH:13]C=[CH:11][CH:10]=1.[C:18](=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1>[CH3:18][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 78054-BromotolueneHCID 11430Potassium CarbonateHCID 66827Phenylboronic Acid

Product 1

HCID 125664-MethylbiphenylYield 99%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of the palladium catalyst formed in Example 24 (50 mg), 4-bromotoluene (1.6 mmol), phenyl boronic acid (1.6 mmol) and potassium carbonate (2.4 mmol) in xylene (10 ml) was warmed at 110° C. with stirring for 1 hour. The mixture was filtered and the solid washed with ether. The combined organic extracts were washed with water, dried and then concentrated to give 4-methyl biphenyl in 99% yield. The filtered solid was returned to the reaction flask and further 4-bromotoluene (1.6 mmol), phenyl boronic acid (1.6 mmol) and potassium carbonate (2.4 mmol) in xylene (10 ml) was added and the process repeated to give 4-methyl biphenyl in 99% yield.

Workup

  1. additionwas added

Sources & evidence

ORD record
ord-c51ff9dbd1584d3e9dfbb52774eb5a00
Source dataset
uspto-grants-2012_04
Patent number
US08148562B2

Reaction notes

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