Potassium Carbonate → 3,4'-Dimethoxybiphenyl

HRID 1943533Notes

Reaction equation

HRID 1943533 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10](=[O:13])([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:8][C:5]1[CH:4]=[C:3]([C:2]2[CH:7]=[CH:6][C:5]([O:13][CH3:10])=[CH:4][CH:3]=2)[CH:2]=[CH:7][CH:6]=1

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 696764-Iodoanisole

Product 1

HCID 6118463,4'-DimethoxybiphenylYield 185.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 74236Tetrabutylammonium BromideCatalystHCID 86587398Ethanol toluene waterSolvent

Procedure

A mixture of a mixed solvent (toluene/ethanol/water=1.5/1.5/1; 900 ml), the compound (T-2) (48.6 g, 319.6 mmol), 1-iodo-4-methoxybenzene (68.0 g, 290.6 mmol), 5% palladium on carbon (3.40 g), potassium carbonate (60.2 g, 435.9 mmol) and tetrabutylammonium bromide (23.4 g, 72.7 mmol) was refluxed with stirring for 15 hours under an atmosphere of nitrogen. The resulting reaction mixture was extracted with toluene (400 mL) three times, and the organic layers were washed with water. After the organic layer had been dried over anhydrous magnesium sulfate, the organic solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: toluene), and then by recrystallization from a mixed solvent of heptane, methanol and ethyl acetate to give colorless crystals (57.8 g) of 3,4′-dimethoxybiphenyl (T-3).

Workup

  1. customThe resulting reaction mixture
  2. extractionwas extracted with toluene (400 mL) three times
  3. washthe organic layers were washed with water
  4. dry with materialAfter the organic layer had been dried over anhydrous magnesium sulfate
  5. distillationthe organic solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (eluent: toluene)
  7. customby recrystallization from a mixed solvent of heptane, methanol and ethyl acetate

Sources & evidence

ORD record
ord-a0be07a526d64b44984dc0ef4339204c
Source dataset
uspto-grants-2013_03
Patent number
US08394468B2

Reaction notes

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