Dimethylformamide → 2-Methoxy-6-methylbenzonitrile

HRID 1466070Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1466070
Br[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[O:9][CH3:10].[C:11]([Cu])#[N:12].CN(C=O)C>C(Cl)Cl>[CH3:10][O:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[C:11]#[N:12]

Komponenten

5

Edukt 3

HCID 6228DimethylformamideHCID 117902332-Bromo-3-methoxytolueneHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 5902262-Methoxy-6-methylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a flask containing a stir bar was added 2-bromo-1-methoxy-3-methylbenzene (7.5 g, 37 mmol), CuCN (6.7 g, 75 mmol) followed by addition of DMF (60 mL); the resulting mixture was then refluxed at 150° C. overnight. When the reaction was complete, as evidenced by LC analysis, the reaction flask was taken out of the oil bath and cooled to room temperature. To the reaction mixture was then poured DCM (20 mL) and a precipitate formed immediately. The solids were filtered, re-dissolved in DCM, absorbed into silica gel and loaded into column with Hexanes:EtOAc (1:1) to afford the title product.

Aufarbeitung

  1. additionTo a flask containing a stir bar
  2. temperaturecooled to room temperature
  3. filtrationThe solids were filtered
  4. dissolutionre-dissolved in DCM
  5. customabsorbed into silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e19fa2fd3d2f4c63a78c51bbbc15e8eb
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999990B2

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