Sodium Carbonate → (2-Ethyl-4'-methoxy-1,1'-biphenyl-4-yl)acetonitrile

HRID 2076629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2076629
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]#[N:15])=[CH:9][C:8]=1[CH2:16][CH3:17])(=O)=O.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1.C(=O)([O-])[O-].[Na+].[Na+]>>[CH2:16]([C:8]1[CH:9]=[C:10]([CH2:13][C:14]#[N:15])[CH:11]=[CH:12][C:7]=1[C:25]1[CH:26]=[CH:27][C:22]([O:21][CH3:20])=[CH:23][CH:24]=1)[CH3:17]

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 860880834-(Cyanomethyl)-2-ethylphenyl trifluoromethanesulfonate

Produkt 1

HCID 67119130(2-Ethyl-4'-methoxy-1,1'-biphenyl-4-yl)acetonitrileAusbeute 66,3 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

After toluene (150 ml), ethanol (30 ml) and distilled water (30 ml) were added to 4-(cyanomethyl)-2-ethylphenyl trifluoromethanesulfonate (9.7 g, 33 mmol) obtained in Example (26-2), 4-methoxyphenylboronic acid (5.3 g, 35 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (2.7 g, 3.3 mol) and sodium carbonate (10.0 g, 94 mmol), the mixture was stirred at 80° C. for 4 hours. After the reaction mixture was cooled to room temperature, the insolubles were removed by filtration. The obtained filtrate was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=7/1-6/1) to give (2-ethyl-4′-methoxy-1,1′-biphenyl-4-yl)acetonitrile as an oil (5.5 g, yield: 66%).

Aufarbeitung

  1. distillationAfter toluene (150 ml), ethanol (30 ml) and distilled water (30 ml)
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. customthe insolubles were removed by filtration
  4. additionThe obtained filtrate was poured into water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was successively washed with water
  7. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  8. customThe residue obtained
  9. customby removing the solvent under reduced pressure
  10. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=7/1-6/1)

Quellen und Nachweise

ORD-Eintrag
ord-317b4849aa174d758edea0d47abf949f
Quelldatensatz
uspto-grants-2011_04
Patentnummer
US07923573B2

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