N-bromobutanimide → 5-Bromo-2-(bromomethyl)benzonitrile

HRID 1921320ノート

反応式

HRID 1921320 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:10])=[C:6]([CH:9]=1)[C:7]#[N:8].[Br:11]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][Br:11])=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

4

反応物 2

HCID 67184N-bromobutanimideHCID 129940045-Bromo-2-methylbenzonitrile

生成物 1

HCID 442031405-Bromo-2-(bromomethyl)benzonitrile収率 38.4%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

A mixture of 5-bromo-2-methylbenzonitrile (5.0 g, 25.5 mmol), N-bromosuccinimide (4.54 g, 25.5 mmol), 2′,2′-azobis(2-methylpropionitrile) (0.05 g) and carbon tetrachloride (25 mL) is heated at reflux for 75 min. After cooling to room temperature, the solids are removed by filtration. The filtrate is concentrated and the residue purified by chromatography eluting with cyclohexane-20% ethyl acetate. Product containing fractions are combined and concentrated to afford 5-bromo-2-bromomethylbenzonitrile (2.69 g, 38%). LC/MS: MS showed no parent molecular ion peak; RT 3.52 min.

後処理

  1. temperatureis heated
  2. temperatureat reflux for 75 min
  3. customthe solids are removed by filtration
  4. concentrationThe filtrate is concentrated
  5. customthe residue purified by chromatography
  6. washeluting with cyclohexane-20% ethyl acetate
  7. additionProduct containing fractions
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-88b50ee940064fe38590d9e5f5760b69
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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