Benzoyl Peroxide → (E)-4-bromo-3-phenoxy-but-2-enoic acid ethyl ester

HRID 19295ノート

反応式

HRID 19295 の反応式
[CH2:1]([O:3][C:4](=[O:15])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)\[CH3:7])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)\[CH2:7][Br:16])[CH3:2]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5356939(E)-3-phenoxy-but-2-enoic acid ethyl ester

生成物 1

HCID 66895145(E)-4-bromo-3-phenoxy-but-2-enoic acid ethyl ester収率 74.5%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a stirred mixture of (E)-3-phenoxy-but-2-enoic acid ethyl ester (5.00 g, 0.024 mol) in carbon tetrachloride (20 mL) under a nitrogen atmosphere was added N-bromosuccinimide (6.50 g, 0.037 mol) and benzoyl peroxide (580 mg, 0.002 mol). Nitrogen gas was bubbled through the mixture for 5 min, and the resulting mixture was heated to reflux for 4 h. The reaction mixture was then placed in the refrigerator overnight. The solids formed were removed by filtration and the filtrate concentrated in vacuo. The crude product obtained was purified using flash column chromatography (silica gel (100-200 mesh), ethyl acetate/hexanes) to afford (E)-4-bromo-3-phenoxy-but-2-enoic acid ethyl ester (5.10 g, 74%) as a yellow oil.

後処理

  1. customNitrogen gas was bubbled through the mixture for 5 min
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 4 h
  4. customwas then placed in the refrigerator overnight
  5. customThe solids formed
  6. customwere removed by filtration
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe crude product obtained
  9. customwas purified

出典と根拠

ORDレコード
ord-137bc97d158748f98a9f507b3ca5d1fc
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

読み込み中…