Benzoyl Peroxide → 4-Bromo-3-(4-methoxy-phenoxy)-but-2-enoic acid ethyl ester

HRID 19066ノート

反応式

HRID 19066 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][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[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:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)[CH2:7][Br:18])[CH3:2]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 668947953-(4-Methoxy-phenoxy)-but-2-enoic acid ethyl ester

生成物 1

HCID 668954354-Bromo-3-(4-methoxy-phenoxy)-but-2-enoic acid ethyl ester収率 78.4%

試薬・触媒・溶媒 1

HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
25 °C

実験手順

A solution of 3-(4-methoxy-phenoxy)-but-2-enoic acid ethyl ester (0.98 g, 4.17 mmol) in carbon tetrachloride (23.2 mL) was treated with N-bromosuccinimide (0.81 g, 4.59 mmol) and benzoyl peroxide (81 mg, 0.33 mmol). The reaction was then heated to reflux for 5 h. At this time, the reaction was cooled to 25° C. and then was placed in the freezer over the weekend. At this time, the reaction was removed from the freezer and allowed to thaw. The resulting precipitate was removed by filtration and was rinsed with carbon tetrachloride (5 mL). The filtrate was concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 1-4% ethyl acetate/hexanes) afforded impure 4-bromo-3-(4-methoxy-phenoxy)-but-2-enoic acid ethyl ester (1.03 g, 78%) as a pale, yellow oil. The material was used without further purification.

後処理

  1. temperatureThe reaction was then heated
  2. temperatureto reflux for 5 h
  3. customAt this time, the reaction was removed from the freezer
  4. customThe resulting precipitate was removed by filtration
  5. washwas rinsed with carbon tetrachloride (5 mL)
  6. concentrationThe filtrate was concentrated in vacuo
  7. customPurification by Analogix flash chromatography (40 g, 1-4% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-007e44bde25340908035797ba6283bda
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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