Ammonia → 3,4-Diethoxy-2-fluorobenzonitrile

HRID 2223755Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2223755
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH3:13])=[C:7]([O:14][CH2:15][CH3:16])[C:6]=1[F:17].C(OCC)(=O)C.N>CN(C)C=O>[CH2:15]([O:14][C:7]1[C:6]([F:17])=[C:5]([CH:10]=[CH:9][C:8]=1[O:11][CH2:12][CH3:13])[C:2]#[N:3])[CH3:16]

Komponenten

6

Edukt 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 230937081-Bromo-3,4-diethoxy-2-fluorobenzeneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 230937173,4-Diethoxy-2-fluorobenzonitrileAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
155 °C

Versuchsvorschrift

Copper(I)cyanide (6.8 g, 68.3 mmol) was added to a solution of 1-bromo-3,4-diethoxy-2-fluorobenzene (12.0 g, 45.6 mmol) in N,N-dimethylformamide (DMF) (60 mL) at room temperature, and this was then stirred at 155° C. for 3 hours. The reaction solution was cooled on ice. Following addition of ethyl acetate and 28% aqueous ammonia, the organic layer was separated and washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was removed after filtration, and the residue was purified by silica gel column chromatography (n-hexane, ethyl acetate) to give 9.0 g of the subject compound (yield: 94.3%).

Aufarbeitung

  1. temperatureThe reaction solution was cooled on ice
  2. customthe organic layer was separated
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed
  6. filtrationafter filtration
  7. customthe residue was purified by silica gel column chromatography (n-hexane, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-658744872cee4cc89b01c6b862acc909
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07375236B2

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