Azobisisobutyronitrile → 2-(Bromomethyl)-3-chlorobenzonitrile

HRID 1886463

反応式

HRID 1886463 の反応式
[Cl:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[Br:11]N1C(=O)CCC1=O.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:4]([C:5]#[N:6])[C:3]=1[CH2:10][Br:11]

参加物

6

反応物 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 5215083-Chloro-2-methylbenzonitrile

生成物 1

HCID 149805102-(Bromomethyl)-3-chlorobenzonitrile収率 46%

試薬・触媒・溶媒 2

HCID 5943Carbon Tetrachloride溶媒HCID 6344Dichloromethane溶媒

実験手順

To a refluxing solution of 3-chloro-2-methylbenzonitrile (2.0 g, 13.2 mmol) in 20 mL of CCl4 was added 2.6 g (14.4 mmol, 1.1 eq) of N-bromosuccinimide and 0.2 g of AIBN. The solution was refluxed for 3 hours and then cooled, diluted with 500 mL of CH2Cl2 and washed with 200 mL of H2O and 200 mL of brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resultant oil was flash chromatographed with 5:1 hexane/ethyl acetate to yield the titled compound (1.4 g, 46%) as a yellow oil.

後処理

  1. temperatureThe solution was refluxed for 3 hours
  2. temperaturecooled
  3. washwashed with 200 mL of H2O and 200 mL of brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customchromatographed with 5:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-4280b87baf5245388b53ad9905af87bd
出典データセット
uspto-grants-1992_09
特許番号
US05151435

関連ノート

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