Isobutyronitrile → 2-Methyl-2-phenylpropanenitrile

HRID 44441

反応式

HRID 44441 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-0527e5fadd774f6898b206182be29928
出典データセット
uspto-grants-2013_09
特許番号
US08541431B2

関連ノート

読み込み中…