Azobisisobutyronitrile → 2-(Bromomethyl)-1-benzofuran

HRID 963477Notes

Reaction equation

HRID 963477 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH:6]=1.[Br:11]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:11][CH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 202632-Methyl-1-benzofuranHCID 67184N-bromobutanimide

Product 1

HCID 123263162-(Bromomethyl)-1-benzofuranYield 102.6%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A suspension of 2-methylbenzofuran (0.708 g) and N-bromosuccinimide (0.963 g) in carbon tetrachloride (10 ml) was heated at reflux temperature for 2.5 hours. To the mixture was added 2,2'-azobis(isobutyronitrile) (0.1 g) and heated at the same temperature for additional 1 hour. The reaction mixture was allowed to cool to room temperature. The resultant precipitates were filtered off by suction. The filtrate was concentrated in vacuo to give 2-bromomethylbenzofuran (1.16 g), which was used in a following reaction step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2.5 hours
  3. temperatureheated at the same temperature for additional 1 hour
  4. customThe resultant precipitates
  5. filtrationwere filtered off by suction
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-1c5abc2a5f604653ac7d6f4ed1574675
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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