Azobisisobutyronitrile → Methyl 4-(bromomethyl)-4'-nitrobiphenyl-3-carboxylate

HRID 403698

Reaktionsgleichung

Reaktionsgleichung von HRID 403698
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][C:3]=1[C:17]([O:19][CH3:20])=[O:18].CC(N=NC(C#N)(C)C)(C#N)C.C1C(=O)N([Br:40])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:40][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)=[CH:4][C:3]=1[C:17]([O:19][CH3:20])=[O:18]

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 67307694Methyl 4-methyl-4'-nitrobiphenyl-3-carboxylate

Produkt 1

HCID 67306641Methyl 4-(bromomethyl)-4'-nitrobiphenyl-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The compound of example 3 (5.7 g, 0.021 mol) was dissolved in carbon tetrachloride (125 mL). AIBN (350 mg) and NBS (4.1 g, 0.0231 mol) were added and the reaction mixture was refluxed at 80° C. After completion of the reaction, the reaction mixture was cooled to room temperature and filtered through celite. The filtrate was concentrated to obtain a crude material containing 85% mono bromo and 10% dibromo product and 5% starting material. The crude was used directly without purification for the preparation of the compound of example 5.

Aufarbeitung

  1. customAfter completion of the reaction
  2. temperaturethe reaction mixture was cooled to room temperature
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-7566dc0364ba4d0e8bd6b284ae59ec52
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748426B2

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