N-bromobutanimide → 4-Bromo-3-(2,4-difluoro-phenoxy)-but-2-enoic acid ethyl ester

HRID 19084ノート

反応式

HRID 19084 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]([F:15])=[CH:11][C:10]=1[F:16])[CH3:7])[CH3:2].[Br:18]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[CH:5]=[C:6]([O:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=1[F:16])[CH2:7][Br:18])[CH3:2]

参加物

5

反応物 2

HCID 67184N-bromobutanimideHCID 668948693-(2,4-Difluoro-phenoxy)-but-2-enoic acid ethyl ester

生成物 1

HCID 668948514-Bromo-3-(2,4-difluoro-phenoxy)-but-2-enoic acid ethyl ester収率 81.1%

試薬・触媒・溶媒 2

HCID 7187Benzoyl Peroxide触媒HCID 5943Carbon Tetrachloride溶媒

反応条件

温度
105 °C

実験手順

A solution of 3-(2,4-difluoro-phenoxy)-but-2-enoic acid ethyl ester (1.35 g, 5.57 mmol) in carbon tetrachloride (30.9 mL) was treated with N-bromosuccinimide (1.09 g, 6.13 mmol) and benzoyl peroxide (108 mg, 0.44 mmol). The reaction was then heated to reflux (105° C.) for 5 h. At this time, the reaction was cooled to 25° C. and then was placed in the refrigerator overnight. At this time, the reaction was removed from the refrigerator. The resulting precipitate was removed by filtration and was rinsed with carbon tetrachloride (10 mL). The filtrate was concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 2% ethyl acetate/hexanes) afforded impure 4-bromo-3-(2,4-difluoro-phenoxy)-but-2-enoic acid ethyl ester (1.45 g, 81%) as a clear oil. The material was used without further purification.

後処理

  1. temperatureThe reaction was then heated
  2. temperatureAt this time, the reaction was cooled to 25° C.
  3. customwas placed in the refrigerator overnight
  4. customAt this time, the reaction was removed from the refrigerator
  5. customThe resulting precipitate was removed by filtration
  6. washwas rinsed with carbon tetrachloride (10 mL)
  7. concentrationThe filtrate was concentrated in vacuo
  8. customPurification by Analogix flash chromatography (40 g, 2% ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-0a80e382673545c78d2bfafe49f2062d
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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