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

HRID 19217

Reaktionsgleichung

Reaktionsgleichung von HRID 19217
[CH2:1]([O:3][C:4](=[O:19])/[CH:5]=[C:6](/[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([CH3:18])([CH3:17])[CH3:16])\[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]=[CH:11][C:10]=1[C:15]([CH3:18])([CH3:17])[CH3:16])\[CH2:7][Br:20])[CH3:2]

Komponenten

5

Edukt 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 67504254(E)-3-(2-t-butyl-phenoxy)-but-2-enoic acid ethyl ester

Produkt 1

HCID 67504522(E)-4-bromo-3-(2-t-butyl-phenoxy)-but-2-enoic acid ethyl esterAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a stirred mixture of (E)-3-(2-t-butyl-phenoxy)-but-2-enoic acid ethyl ester (3.20 g, 0.012 mol) in carbon tetrachloride (20 mL) under a nitrogen atmosphere was added N-bromosuccinimide (3.26 g, 0.018 mol) and benzoyl peroxide (295 mg, 0.001 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-(2-t-butyl-phenoxy)-but-2-enoic acid ethyl ester (2.10 g, 50%) 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-bb3f25397f944f85a7a90471a6a73096
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741327B2

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