تفاعل #8198

ord-891086c3a8cc43c7beb58f68c0a282e1

معادلة التفاعل

Cc1csc2ccccc12
3-Methylbenzo[b]thiophene
O=C1CCC(=O)N1Br
n-bromosuccinimide
CC(C)(C#N)N=NC(C)(C)C#N
2,2′Azobisisobutyronitrile
BrCc1csc2ccccc12
3-Bromomethylbenzo[b]thiophene
المردود 42.2%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthe resulting mixture is refluxed for two hours
  2. 2
    درجة الحرارةAfter cooling
  3. 3
    ترشيحthe reaction mixture is filtered through a glass-fritted funnel
  4. 4
    تركيزthe filtrate is concentrated
  5. 5
    أخرىThe residue is triturated with petroleum ether and toluene

الإجراء التجريبي

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%).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07087635B2uspto-grants-2006_08