N-bromobutanimide → 4-Bromo-3-(naphthalen-1-yloxy)-but-2-enoic acid ethyl ester
Reaktionsgleichung
[CH2:1]([O:3][C:4](=[O:19])[CH:5]=[C:6]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH3:7])[CH3:2].[Br:20]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:19])[CH:5]=[C:6]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][CH:10]=1)[CH2:7][Br:20])[CH3:2]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 25 °C
Versuchsvorschrift
A solution of 3-(naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (1.15 g, 4.48 mmol) in carbon tetrachloride (24.9 mL) was treated with N-bromosuccinimide (0.87 g, 4.93 mmol) and benzoyl peroxide (87 mg, 0.35 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, 2% ethyl acetate/hexanes) afforded impure 4-bromo-3-(naphthalen-1-yloxy)-but-2-enoic acid ethyl ester (1.28 g, 85%) as a light purple oil. The material was used without further purification.
Aufarbeitung
- temperatureThe reaction was then heated
- temperatureto reflux for 5 h
- customAt this time, the reaction was removed from the freezer
- customThe resulting precipitate was removed by filtration
- washwas rinsed with carbon tetrachloride (5 mL)
- concentrationThe filtrate was concentrated in vacuo
- customPurification by Analogix flash chromatography (40 g, 2% ethyl acetate/hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-8ef2a6d320ad4fabb4edd1822db43281
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07741327B2
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