Benzoyl Peroxide → (E)-4-bromo-3-(3-methoxy-phenoxy)-but-2-enoic acid ethyl ester

HRID 19270Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 19270
[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]([O:15][CH3:16])[CH:10]=1)\[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]([O:15][CH3:16])[CH:10]=1)\[CH2:7][Br:18])[CH3:2]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 66894839(E)-3-(3-methoxy-phenoxy)-but-2-enoic acid ethyl ester

Produkt 1

HCID 66894498(E)-4-bromo-3-(3-methoxy-phenoxy)-but-2-enoic acid ethyl esterAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred mixture of (E)-3-(3-methoxy-phenoxy)-but-2-enoic acid ethyl ester (5.50 g, 0.023 mol) in carbon tetrachloride (20 mL) under a nitrogen atmosphere was added N-bromosuccinimide (6.22 g, 0.035 mol) and benzoyl peroxide (563 mg, 0.002 mol). Nitrogen gas was bubbled through the mixture for 5 min, and the resulting mixture was heated to reflux for 4 h. The reaction mixture was then placed in the refrigerator overnight. The solids formed were removed by filtration and the filtrate concentrated in vacuo. The crude product obtained was purified using flash column chromatography (silica gel (100-200 mesh), ethyl acetate/hexanes) to afford (E)-4-bromo-3-(3-methoxy-phenoxy)-but-2-enoic acid ethyl ester (4.00 g, 55%) as a yellow oil.

Aufarbeitung

  1. customNitrogen gas was bubbled through the mixture for 5 min
  2. temperaturethe resulting mixture was heated
  3. temperatureto reflux for 4 h
  4. customwas then placed in the refrigerator overnight
  5. customThe solids formed
  6. customwere removed by filtration
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe crude product obtained
  9. customwas purified

Quellen und Nachweise

ORD-Eintrag
ord-d16a5bf1c8b44ea39a3af05683e128de
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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