Azobisisobutyronitrile → 3-(Bromomethyl)-1-benzothiophene

HRID 1072597

Reaction equation

HRID 1072597 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 112646413-(Bromomethyl)-1-benzothiopheneYield 42.2%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

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%). The title amine is prepared from 3-(bromomethyl)-benzo[B]thiophene in a similar fashion as described in U.S. Pat. No. 4,321,398.

Workup

  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

Sources & evidence

ORD record
ord-72b57041208a4f0189159b5c6e89268c
Source dataset
uspto-grants-2005_06
Patent number
US06911463B2

Linked notes

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