Azobisisobutyronitrile → Methyl 2-acetoxy-4-(bromomethyl)benzoate

HRID 1739464Notes

Reaction equation

HRID 1739464 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[C:1]([O:4][C:5]1[CH:14]=[C:13]([CH2:15][Br:16])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21841044Methyl 2-acetoxy-4-methylbenzoate

Product 1

HCID 21840999Methyl 2-acetoxy-4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A solution of methyl 2-acetoxy-4-methylbenzoate (24.5 g, 0.118 mole) in carbon tetrachloride (700 ml) was treated with N-bromosuccinimide (20.96 g, 0.118 mole), benzoyl peroxide (0.5 g, catalytic) and AIBN (0.03 g). The reaction mixture was heated to reflux, held at reflux for 1 hour and then allowed to cool to ambient temperature, filtered and evaporated to give methyl 2-acetoxy-4-bromomethylbenzoate which was used without further purification (34 g, 63% of mixture is desired product).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. temperatureat reflux for 1 hour
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-160b23fdf5394539a474a5e4a51e194f
Source dataset
uspto-grants-1999_10
Patent number
US05965741

Reaction notes

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