Azobisisobutyronitrile → 3-(Bromomethyl)-1-benzothiophene

HRID 1272222

Reaction equation

HRID 1272222 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%).

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-60dcc74147ce49ca9e0d702b0b0b53ad
Source dataset
uspto-grants-2007_04
Patent number
US07208505B2

Linked notes

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