Isobutyronitrile → 2-Methyl-2-phenylpropanenitrile
Reaction equation
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]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of fluorobenzene (5.85 mL, 62.4 mmol) in 100 mL of anhydrous toluene is 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 is then stirred at 80° C. for 24 hours. The reaction is then allowed to cool to room temperature, diluted with diethyl ether, and washed with water and brine. The organic fraction is then dried over sodium sulfate and concentrated under reduced pressure. The product is purified by flash chromatography using an ethyl acetate/hexanes gradient to yield 4.57 g (50% yield) 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).
Workup
- temperatureto cool to room temperature
- washwashed with water and brine
- dry with materialThe organic fraction is then dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe product is purified by flash chromatography
Sources & evidence
- ORD record
- ord-f8e3f6cc77054fc98312e9c460613044
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08431595B2
Reaction notes
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