Azobisisobutyronitrile → 2-(Bromomethyl)-6-chlorobenzonitrile

HRID 1752245ノート

反応式

HRID 1752245 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl.ClCCl>[Br:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:2]([Cl:1])[C:3]=1[C:4]#[N:5]

参加物

6

反応物 3

HCID 6547AzobisisobutyronitrileHCID 230532-Chloro-6-methylbenzonitrileHCID 67184N-bromobutanimide

生成物 1

HCID 667339472-(Bromomethyl)-6-chlorobenzonitrile収率 46.7%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-chloro-6-methylbenzonitrile (2.0 g, 13 mmol) and N-bromosuccinimide (2.6 g, 15 mmol) in carbon tetrachloride (20 mL) was added azobisisobutyronitrile (0.20 g, 1.2 mmol). The mixture was refluxed for 3 h and then cooled, diluted with dichloromethane and washed with water and brine. The organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70) to yield white solid product (1.4 g, 46%). 1H NMR (400 MHz, CDCl3) δ 7.43-7.59 (m, 3H), 4.64 (s, 2H).

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. temperaturecooled
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resultant oil was purified via flash column chromatography (ethyl acetate:hexane, 0:100 to 30:70)

出典と根拠

ORDレコード
ord-15bbc06972cc442d96d857f173004298
出典データセット
uspto-grants-2015_10
特許番号
US09163003B2

反応ノート

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