Azobisisobutyronitrile → Ethyl 2-(bromomethyl)benzoate

HRID 660557Notes

Reaction equation

HRID 660557 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11])[CH3:2].[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][Br:13])[CH3:2]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 66598Ethyl 2-methylbenzoateHCID 67184N-bromobutanimide

Product 1

HCID 11032082Ethyl 2-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-methylbenzoic acid ethyl ester (16.4 g, 99.87 mmol) in CCl4 (100 mL) is added N-bromosuccinimide (17.8 g, 100 mmol) and 2,2′-azobisisobutyronitrile (3.28 g, 19.97 mmol). The resulting mixture is heated at reflux for 2 h. After the mixture is cooled to RT, the solid is filtered off and the filtrate is concentrated and extracted with EtOAc. The EtOAc solution is washed with brine and dried over MgSO4, filtered and concentrated to afford the title compound as a pale yellow oil.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 2 h
  3. filtrationthe solid is filtered off
  4. concentrationthe filtrate is concentrated
  5. extractionextracted with EtOAc
  6. washThe EtOAc solution is washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2da172bca2e544198fcd047b918027ff
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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