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

HRID 19054ノート

反応式

HRID 19054 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]([Cl:15])[C:10]=1[F: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]([Cl:15])[C:10]=1[F:16])[CH2:7][Br:18])[CH3:2]

参加物

5

反応物 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 668948903-(3-Chloro-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester

生成物 1

HCID 668953114-Bromo-3-(3-chloro-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester収率 86.4%

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-(3-chloro-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester (1.41 g, 5.45 mmol) in carbon tetrachloride (30 mL) was treated with N-bromosuccinimide (1.07 g, 6.01 mmol) and benzoyl peroxide (0.15 g). The reaction was then warmed to reflux for 5 h. At this time, the reaction was cooled to 25° C. and then 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. The filtrate was concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes) afforded impure 4-bromo-3-(3-chloro-2-fluoro-phenoxy)-but-2-enoic acid ethyl ester (1.59 g, 86%) as a white solid. The material was used without further purification.

後処理

  1. temperatureThe reaction was then warmed
  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. concentrationThe filtrate was concentrated in vacuo
  6. customPurification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-90743fa93f484cdf8377947ed34feb74
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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