Isobutyronitrile → 2-Methyl-2-phenylpropanenitrile

HRID 44441

Reaktionsgleichung

Reaktionsgleichung von HRID 44441
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8](#[N:12])[CH:9]([CH3:11])[CH3:10].C[Si]([N-][Si](C)(C)C)(C)C.[K+]>C1(C)C=CC=CC=1.C(OCC)C>[CH3:10][C:9]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:11])[C:8]#[N:12]

Komponenten

6

Edukt 3

HCID 6559IsobutyronitrileHCID 10008FluorobenzeneHCID 3251421Potassium bis(trimethylsilyl)amide

Produkt 1

HCID 27975912-Methyl-2-phenylpropanenitrileAusbeute 50,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittel2×HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of fluorobenzene (5.85 mL, 62.4 mmol) in 100 mL of anhydrous toluene was added isobutyronitrile (22.5 mL, 250 mmol) followed by 200 mL (100 mmol) of a 0.5 M solution of KHMDS in toluene. The reaction was stirred at 80° C. for 24 hours. The reaction was then allowed to cool to room temperature, diluted with diethyl ether, and washed with water and brine. The organic fraction was dried over sodium sulfate and concentrated under reduced pressure. The product was purified by flash chromatography using an ethyl acetate/hexanes gradient to yield 4.57 g (50%) of the objective compound as a brown oil. MS: (ESI, Pos) m/z 168.0 (M+23). 1H NMR (500 MHz, CDCl3): δ (ppm) 7.48 (d, 2H), 7.39 (t, 2H), 7.31 (t, 1H), 1.73 (s, 6H).

Aufarbeitung

  1. temperatureto cool to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic fraction was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0527e5fadd774f6898b206182be29928
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541431B2

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