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

HRID 19251ノート

反応式

HRID 19251 の反応式
[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[CH3:16])\[CH3:7])[CH3:2].[Br:18]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:17])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[CH3:16])\[CH2:7][Br:18])[CH3:2]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66894788(E)-3-(2,3-dimethyl-phenoxy)-but-2-enoic acid ethyl ester

生成物 1

HCID 66895041(E)-4-bromo-3-(2,3-dimethyl-phenoxy)-but-2-enoic acid ethyl ester収率 31%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

実験手順

To a stirred mixture of (E)-3-(2,3-dimethyl-phenoxy)-but-2-enoic acid ethyl ester (7.19 g, 0.031 mol) in carbon tetrachloride (40 mL) under a nitrogen atmosphere was added N-bromosuccinimide (8.19 g, 0.046 mol) and benzoyl peroxide (730 mg, 0.003 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-(2,3-dimethyl-phenoxy)-but-2-enoic acid ethyl ester (3.00 g, 31%) 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-543c4f38b7b24166b70824adaba1bc3c
出典データセット
uspto-grants-2010_06
特許番号
US07741327B2

反応ノート

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