Azobisisobutyronitrile → 3-(Bromomethyl)-1-benzothiophene

HRID 1272222

Reaktionsgleichung

Reaktionsgleichung von HRID 1272222
[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-60dcc74147ce49ca9e0d702b0b0b53ad
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208505B2

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