Azobisisobutyronitrile → [2-(Bromomethyl)phenyl]acetic acid

HRID 397474Notes

Reaction equation

HRID 397474 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9].[Br:12]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:12][CH2:11][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 69519o-Tolylacetic acid

Product 1

HCID 12889260[2-(Bromomethyl)phenyl]acetic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
2.5 °C

Procedure

To a solution of 97.0 g (0.646 mol) o-tolylacetic acid in 1.75 L carbon tetrachloride was added 115.0 g (0.646 mol) N-bromosuccinimide and 3.4 g (0.021 mol) 2,2′-azobisisobutyronitrile. The mixture was heated at reflux under a nitrogen atmosphere for 4 h. After the mixture was cooled to 0-5° C. for 30 min, the solids were removed by filtration and washed with a small portion of carbon tetrachloride. This solid was triturated with water (0.8 L), collected on a filter, and washed with 500 mL of water to give 2-bromomethylphenylacetic acid. The filtrate was concentrated to a volume of 150 ml, and the resulting slurry cooled to 0-5° C. for 30 min. A second batch of product was obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux under a nitrogen atmosphere for 4 h
  3. customthe solids were removed by filtration
  4. washwashed with a small portion of carbon tetrachloride
  5. customThis solid was triturated with water (0.8 L)
  6. customcollected on a filter
  7. washwashed with 500 mL of water

Sources & evidence

ORD record
ord-5ed4eef8a2f948d1bf8076ec627e03c8
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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