3-Bromo-5-formylbenzamide → 3-Bromo-5-formylbenzonitrile

HRID 562287ノート

反応式

HRID 562287 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[C:5]([NH2:7])=O>O.CC#N.Cl[Pd]Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH:11]=[O:12])[CH:10]=1)[C:5]#[N:7]

参加物

5

反応物 1

HCID 866310333-Bromo-5-formylbenzamide

生成物 1

HCID 534255233-Bromo-5-formylbenzonitrile収率 40%

試薬・触媒・溶媒 3

HCID 24290Palladium Chloride触媒2 回HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒2 回

実験手順

To a solution of 3-bromo-5-formylbenzamide (1.5 g, 6.58 mmol) in H2O (50.0 mL) and MeCN (50.0 mL) was added PdCl2 (117 mg, 0.658 mmol). The mixture was stirred for 72 h at room temperature and another portion of H2O (100 mL) and MeCN (100 mL) was added followed with addition of PdCl2 (100 mg, 0.56 mol). The mixture was stirred for another 12 hr and concentrated. The residue was dissolved in EtOAc (200 mL), washed with brine (3×50.0 mL), dried over Na2SO4 and concentrated, and then was purified by chromatography (10% EtOAc in hexanes) to give 550 mg of 3-bromo-5-formylbenzonitrile (40%).

後処理

  1. stirringThe mixture was stirred for another 12 hr
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in EtOAc (200 mL)
  4. washwashed with brine (3×50.0 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customwas purified by chromatography (10% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-cbc6ae822ead4af3a2d3a9b8609752df
出典データセット
uspto-grants-2011_11
特許番号
US08063071B2

反応ノート

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