Butyl bromide → 4-Butoxy-3-methoxybenzonitrile

HRID 1801477

Reaktionsgleichung

Reaktionsgleichung von HRID 1801477
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]#[N:10])[CH:6]=[CH:5][C:4]=1[OH:11].C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[CH2:19][CH2:20][CH3:21]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:6]=[CH:5][C:4]=1[O:11][CH2:18][CH2:19][CH2:20][CH3:21])[C:9]#[N:10]

Komponenten

5

Edukt 3

HCID 8002Butyl bromideHCID 11430Potassium CarbonateHCID 781354-Hydroxy-3-methoxybenzonitrile

Produkt 1

HCID 44587574-Butoxy-3-methoxybenzonitrileAusbeute 105,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
37 °C

Versuchsvorschrift

2-methoxy-4-cyano-phenol (0.25 g, 1.67 mmol) and anhydrous DMF (2.00 mL) were added into a flask, then cooled in a water bath while stirring. Several batches of K2CO3 (0.347 g, 2.50 mmol) were added to the mixture and stirred at 20° C. to react for 1 h. n-butyl bromine (0.23 ml, 2.14 mmol) was added into the mixture, which was stirred at room temperature overnight, then heated at 37° C. to react for 6 h. Poured the solution into a mixture of ice/H2O (25 mL), then stirred for 10 min, a precipitate was formed. Filtered, washed with H2O, and air-dried to yield 0.361 g of white solid product with a recovery rate of 92%.

Aufarbeitung

  1. temperaturecooled in a water bath
  2. stirringstirred at 20° C.
  3. additionwas added into the mixture, which
  4. stirringwas stirred at room temperature overnight
  5. customto react for 6 h
  6. additionPoured the solution
  7. stirringstirred for 10 min
  8. customa precipitate was formed
  9. filtrationFiltered
  10. washwashed with H2O
  11. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-530c5479ce4140b091847314f7dece14
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08349835B2

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