Réaction #8198

Équation de réaction

3-Methylbenzo[b]thiophene

n-bromosuccinimide

2,2′Azobisisobutyronitrile

→

3-Bromomethylbenzo[b]thiophene

Rendement 42.2%

Solvants

carbon tetrachloride

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source