Thionyl Chloride → 5-(Chloromethyl)-2-cyclohexylbenzonitrile

HRID 2040547ノート

反応式

HRID 2040547 の反応式
[CH:1]1([C:7]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][C:8]=2[C:9]#[N:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:19])=O>>[Cl:19][CH2:15][C:12]1[CH:13]=[CH:14][C:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[C:8]([CH:11]=1)[C:9]#[N:10]

参加物

3

反応物 2

HCID 24386Thionyl ChlorideHCID 580205132-Cyclohexyl-5-(hydroxymethyl)benzonitrile

生成物 1

HCID 672113535-(Chloromethyl)-2-cyclohexylbenzonitrile収率 89.4%

反応条件

温度
50 °C

実験手順

To 2-cyclohexyl-5-(hydroxymethyl)benzonitrile (190.5 mg, 0.885 mmol) was added thionyl chloride (5.0 mL, 68.1 mmol). The mixture was heated at 50° C. for 2 h and then room temperature overnight. The mixture was poured into an ice and stirred for 5 min. The mixture was extracted with dichloromethane. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide the title compound as a white solid (184.9 mg). LCMS m/z=234.1 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.31 (m, 1H), 1.40-1.52 (m, 4H), 1.76-1.82 (m, 1H), 1.83-1.92 (m, 4H), 2.93-3.03 (m, 1H), 4.55 (s, 2H), 7.37 (d, J=8.08 Hz, 1H), 7.55 (dd, J=8.02, 1.83 Hz, 1H), 7.62 (d, J=1.64 Hz, 1H).

後処理

  1. customroom temperature overnight
  2. extractionThe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cc83b98607d64fe5902a247ce413cb60
出典データセット
uspto-grants-2013_11
特許番号
US08580841B2

反応ノート

読み込み中…