Isobutyronitrile → 2-Methyl-2-phenylpropanenitrile

HRID 1942121

反応式

HRID 1942121 の反応式
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]

参加物

6

反応物 3

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

生成物 1

HCID 27975912-Methyl-2-phenylpropanenitrile収率 50.4%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 3283Diethyl Ether溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-efc82b1cf5a441138d542df39f2d5dd0
出典データセット
uspto-grants-2013_03
特許番号
US08389534B2

関連ノート

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