Potassium Carbonate → 1,3-bis(4-methoxyphenyl)benzene

HRID 1943534Notes

Reaction equation

HRID 1943534 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[CH:3]=1.[C:9](=[O:12])([O-])[O-].[K+].[K+]>[Pd].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C(O)C.O>[CH3:9][O:12][C:2]1[CH:7]=[CH:6][C:5]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([C:2]3[CH:7]=[CH:6][C:5]([O:12][CH3:9])=[CH:4][CH:3]=3)[CH:3]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 12270Benzene, 1,3-diiodo-

Product 1

HCID 46087621,3-bis(4-methoxyphenyl)benzeneYield 277.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of a mixed solvent (toluene/ethanol/water=5/5/1; 1,600 ml), the compound (T-6) (75.9 g, 499.4 mmol), 1,3-diiodobenzene (75.0 g, 227.3 mmol), 5% palladium on carbon (3.75 g), potassium carbonate (94.1 g, 681.0 mmol) and tetrabutylammonium bromide (18.29 g, 56.7 mmol) was refluxed with stirring for 15 hours under an atmosphere of nitrogen. The resulting reaction mixture was cooled to room temperature, and deposits were collected by filtration. The deposits were recrystallized from a mixed solvent of THF and ethyl acetate to give colorless crystals (61.0 g) of 4,4″-dimethoxy-(1,1′:3′,1″)-terphenyl (T-7).

Workup

  1. customThe resulting reaction mixture
  2. filtrationdeposits were collected by filtration
  3. customThe deposits were recrystallized from a mixed solvent of THF and ethyl acetate

Sources & evidence

ORD record
ord-fad97c459cec4d00824ff02242866704
Source dataset
uspto-grants-2013_03
Patent number
US08394468B2

Reaction notes

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