Azobisisobutyronitrile → Methyl 3-(4-(bromomethyl)phenyl)-2-propenoate

HRID 615502

Reaktionsgleichung

Reaktionsgleichung von HRID 615502
[CH3:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[Br:14]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:1][C:2]1[CH:13]=[CH:12][C:5]([CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 589472Methyl 3-(4-methylphenyl)-2-propenoate

Produkt 1

HCID 53395294Methyl 3-(4-(bromomethyl)phenyl)-2-propenoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 3.0 g (17.03 mmol) of methyl 4-methylcinnamate, 3.33 g (18.73 mmol) of N-bromosuccinimide and 60 mg of 2,2'-azobis(2-methylpropionitrile) in 75 ml of carbon tetrachloride was heated to reflux with a heat lamp and stirred rapidly for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated to give the title compound as an oil which crystallized. NMR in CDCl3 (δ units): 3.80 (singlet, 3); 4.48 (singlet, 2); 6.44 and 7.67 (doublets, J=15 Hz, 1); 7.39, 7.49 (doublets, J=7 Hz, 2).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux with a heat lamp
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-2569c3f546b44b4096345dbd2046f631
Quelldatensatz
uspto-grants-1985_02
Patentnummer
US04499299

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