1-Bromo-2-methylpropane → 4-(2-Methylpropoxy)benzonitrile

HRID 8047

Reaktionsgleichung

Reaktionsgleichung von HRID 8047
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[CH2:17](Br)[CH:18]([CH3:20])[CH3:19]>CN(C=O)C.O>[CH2:17]([O:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[CH:18]([CH3:20])[CH3:19]

Komponenten

6

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 8471TriethylamineHCID 130194-Cyanophenol

Produkt 1

HCID 218937164-(2-Methylpropoxy)benzonitrileAusbeute 85,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 4-cyanophenol (1.2 g, 10 mmol) in dry DMF (20 mL) was added triethylamine (20 mmol) followed by i-butyl bromide (2.7 g, 20 mmol). The resulting reaction mixture was stirred at 100° C. for 6 h. After cooling to room temperature, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (2×40 mL). The organic layer was washed with 4 M KOH (3×30 mL) and then with water, dried over Na2SO4 and concentrated under vacuum to provide 1.5 g (85%) 4-iso-butoxybenzo-nitrile that was used for the next step without further purification. 1H NMR (DMSO-D6): δ 0.95 (d, 6H, 2CH3), 2.0 (m, 1H, CH(CH3)2), 3.8 (d, 2H, CH2), 7.4 (AA′BB′, Δ=20 Hz, 4H, Ar).

Aufarbeitung

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with ethyl acetate (2×40 mL)
  4. washThe organic layer was washed with 4 M KOH (3×30 mL)
  5. dry with materialwith water, dried over Na2SO4
  6. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-178d1c80d262496d81b1b38dcd50183e
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087631B2

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