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

HRID 19048

반응식

HRID 19048 반응식
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=1)[CH3:7])[CH3:2].[Br:20]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:19])[CH:5]=[C:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:16])([F:18])[F:17])[CH:10]=1)[CH2:7][Br:20])[CH3:2]

참가 물질

5

반응물 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 668944643-(3-Trifluoromethyl-phenoxy)-but-2-enoic acid ethyl ester

생성물 1

HCID 668946014-Bromo-3-(3-trifluoromethyl-phenoxy)-but-2-enoic acid ethyl ester수율 83.1%

시약·촉매·용매 1

HCID 5943Carbon Tetrachloride용매

반응 조건

온도
25 °C

실험 절차

A solution of 3-(3-trifluoromethyl-phenoxy)-but-2-enoic acid ethyl ester (1.31 g, 4.77 mmol) in carbon tetrachloride (25 mL) was treated with N-bromosuccinimide (0.94 g, 5.28 mmol) and benzoyl peroxide (0.12 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-trifluoromethyl-phenoxy)-but-2-enoic acid ethyl ester (1.40 g, 83%) as a pale, yellow oil. The material was used without further purification.

후처리

  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)

출처 및 근거

ORD 기록
ord-d9819244923144d88700afc54e615dea
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07741327B2

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