Azobisisobutyronitrile → 3-(Bromomethyl)-1-benzothiophene

HRID 8102

Reaktionsgleichung

Reaktionsgleichung von HRID 8102
[CH3:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.C1C(=O)N([Br:18])C(=O)C1.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:18][CH2:1][C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 738173-Methylbenzo[b]thiophene

Produkt 1

HCID 112646413-(Bromomethyl)-1-benzothiopheneAusbeute 42,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

3-Methylbenzo[b]thiophene (9.9 g, 67 mmol) is heated in carbon tetrachloride (133 ml ) to near reflux in the presence of n-bromosuccinimide (11.9 g, 67 mmol, 1.0 eq.). 2,2′Azobisisobutyronitrile (2.2 g, 13.3 mmol, 0.2 eq.) is added and the resulting mixture is refluxed for two hours. After cooling, the reaction mixture is filtered through a glass-fritted funnel, and the filtrate is concentrated. The residue is triturated with petroleum ether and toluene to afford 6.42 g of 3-Bromomethylbenzo[b]thiophene (42%).

Aufarbeitung

  1. temperaturethe resulting mixture is refluxed for two hours
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered through a glass-fritted funnel
  4. concentrationthe filtrate is concentrated
  5. customThe residue is triturated with petroleum ether and toluene

Quellen und Nachweise

ORD-Eintrag
ord-891086c3a8cc43c7beb58f68c0a282e1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087635B2

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