Azobisisobutyronitrile → 2-(Bromomethyl)-4-chlorobenzonitrile
反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.[Br:11]NC(=O)CCC(N)=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH2:10][Br:11])[CH:3]=1参加物
5
実験手順
To a stirred solution 4-Chloro-2-methyl-benzonitrile 1(5.0 g, 33.0 mmol) in carbon tetrachloride (150 mL) was added N-bromosuccinamide (7.6 g, 42.9 mmol) and 2,2′-azobisisobutyronitrile (cat.). The reaction mixture was refluxed 6 hrs, filtered, concentrated, and partitioned between ether and water. The ether layer was dried, concentrated, and purified by silica gel chromatography (10% ether/hexanes) to yield a white solid (40%). 1H NMR (400 MHz, CDCl3) δ7.61 (d, J=8.3 Hz, 1 H, Ar), 7.57 (d, J=2.2 Hz, 1 H, Ar), 7.41 (dd, J=8.3, 2.0 Hz, 1 H, Ar), 4.59 (s, 2 H, CH2).
後処理
- temperatureThe reaction mixture was refluxed 6 hrs
- filtrationfiltered
- concentrationconcentrated
- custompartitioned between ether and water
- dry with materialThe ether layer was dried
- concentrationconcentrated
- custompurified by silica gel chromatography (10% ether/hexanes)
出典と根拠
- ORDレコード
- ord-51aa161f49f245d7895c5ba0226e0e5d
- 出典データセット
- uspto-grants-2002_04
- 特許番号
- US06376530B1
反応ノート
読み込み中…