Reaktion #8198

Reaktionsgleichung

3-Methylbenzo[b]thiophene

n-bromosuccinimide

2,2′Azobisisobutyronitrile

→

3-Bromomethylbenzo[b]thiophene

Ausbeute 42.2%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resulting mixture is refluxed for two hours
2. 2
   TemperaturAfter cooling
3. 3
   Filtrationthe reaction mixture is filtered through a glass-fritted funnel
4. 4
   Einengenthe filtrate is concentrated
5. 5
   SonstigeThe residue is triturated with petroleum ether and toluene

Vorschrift

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%).

Quelle