Ammonium → 3,4-Diethoxy-2-fluorobenzonitrile

HRID 244331Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 244331
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][CH3:10])=[C:4]([O:11][CH2:12][CH3:13])[C:3]=1[F:14].[Cu][C:16]#[N:17].C(OCC)(=O)C.[NH4+]>CN(C)C=O>[CH2:12]([O:11][C:4]1[C:3]([F:14])=[C:2]([CH:7]=[CH:6][C:5]=1[O:8][CH2:9][CH3:10])[C:16]#[N:17])[CH3:13]

Komponenten

6

Edukt 4

HCID 223AmmoniumHCID 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

To a solution of 1-bromo-3,4-diethoxy-2-fluorobenzene (12.0 g, 45.6 mmoL) in N,N-dimethylformamide (DMF) (60 mL), copper (I) cyanide (6.8 g, 68.3 mmoL) was added at room temperature and then stirred at 155° C. for 3 hours. After ice cooling the reaction solution, ethyl acetate and 28% aqueous ammonium were added thereto to separate the organic layer. This organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated. The residue was purified by silica gel column chromatography (n-hexane, ethyl acetate) to give 9.0 g of the captioned compound (yield: 94.3%).

Aufarbeitung

  1. customto separate the organic layer
  2. washThis organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated
  6. customThe residue was purified by silica gel column chromatography (n-hexane, ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-003d9528fd9c4406a0f00237c8a9d5b2
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658620B2

Notizen zur Reaktion

Wird geladen…