Azobisisobutyronitrile → Ethyl-4-bromo-3-methyl-but-2-enoate (E/Z; 55/45)

HRID 543338Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 543338
[CH3:1][C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[Br:10]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:10][CH2:1][C:2]([CH3:9])=[CH:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]

Komponenten

6

Edukt 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 12516Ethyl 3,3-dimethylacrylateHCID 67184N-bromobutanimide

Produkt 1

HCID 53411540Ethyl-4-bromo-3-methyl-but-2-enoate (E/Z; 55/45)

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To ethyl 3-methyl-2-butenoate (10.0 g, 78.0 mmol) in 80 ml of carbon tetrachloride heated under gentle reflux is added N-bromosuccinimide (15.0 g, 84.0 mmol) in portions, followed by traces of radical initiator (benzoyl peroxide, ca. 0.2 g, and AIBN, ca. 0.1 g) in portions over one hour. After the final addition, the mixture is heated under reflux for 30 min. The reaction mixture is cooled and filtered and the solvent is removed by rotoevaporation to give ethyl 4-bromo-3-methyl-2-butenoate.

Aufarbeitung

  1. temperatureunder gentle reflux
  2. additionAfter the final addition
  3. temperaturethe mixture is heated
  4. temperatureunder reflux for 30 min
  5. temperatureThe reaction mixture is cooled
  6. filtrationfiltered
  7. customthe solvent is removed by rotoevaporation

Quellen und Nachweise

ORD-Eintrag
ord-7172e51f236640dea8e3cdcae4a53782
Quelldatensatz
uspto-grants-1987_04
Patentnummer
US04661617

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