Azobisisobutyronitrile → (6-Bromo-3-bromomethyl-benzofuran-2-yl)(2,4-dichlorophenyl)-methanone

HRID 29246

Reaktionsgleichung

Reaktionsgleichung von HRID 29246
[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH3:19])=[C:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[O:10])[O:8][C:4]=2[CH:3]=1.[Br:22]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH2:19][Br:22])=[C:7]([C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])=[O:10])[O:8][C:4]=2[CH:3]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 59788907(6-Bromo-3-methyl-benzofuran-2-yl)(2,4-dichloro-phenyl)methanone

Produkt 1

HCID 59788888(6-Bromo-3-bromomethyl-benzofuran-2-yl)(2,4-dichlorophenyl)-methanoneAusbeute 78,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of (6-bromo-3-methyl-benzofuran-2-yl)-(2,4-dichloro-phenyl)-methanone (3.0 g, 7.81 mmol) in carbon tetrachloride (30 mL) was added N-bromosuccinimide (1.46 g, 8.2 mmol) and 2,2′-azobisisobutyronitrile (128 mg, 0.78 mmol). The reaction mixture was refluxed for 6 h, then filtered. The filtrate was concentrated and the crude product was triturated with 10% EtOAc/hexane to afford the desired product as a pale yellow solid (2.85 g, 78.9%). This material was used in the subsequent step without further purification.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. customthe crude product was triturated with 10% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-e72283bc9ddc4e078eb8f910a1eef417
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420066B2

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