Potassium Carbonate → 3,4'-Dimethoxybiphenyl

HRID 1943533

Reaktionsgleichung

Reaktionsgleichung von HRID 1943533
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

Komponenten

6

Edukt 2

HCID 11430Potassium CarbonateHCID 696764-Iodoanisole

Produkt 1

HCID 6118463,4'-DimethoxybiphenylAusbeute 185,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 74236Tetrabutylammonium BromideKatalysatorHCID 86587398Ethanol toluene waterLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-a0be07a526d64b44984dc0ef4339204c
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394468B2

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