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

HRID 19048

Reaktionsgleichung

[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]

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

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.

Aufarbeitung

temperatureThe reaction was then warmed
temperatureto reflux for 5 h
customAt this time, the reaction was removed from the freezer
customThe resulting precipitate was removed by filtration
concentrationThe filtrate was concentrated in vacuo
customPurification by Analogix flash chromatography (40 g, 1-10% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag: ord-d9819244923144d88700afc54e615dea
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07741327B2

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