Azobisisobutyronitrile → Methyl 3-bromo-4-(bromomethyl)benzoate

HRID 1937165Notes

Reaction equation

HRID 1937165 reaction equation
CC(N=NC(C#N)(C)C)(C#N)C.[Br:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH3:24])[C:17]([O:19][CH3:20])=[O:18].C1C(=O)N([Br:32])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1[CH2:24][Br:32])[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 7015747Methyl 3-bromo-4-methylbenzoate

Product 1

HCID 10804694Methyl 3-bromo-4-(bromomethyl)benzoateYield 99.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

AIBN (79 mg, 48.0 mmol) was added to a stirred suspension of methyl 3-bromo-4-methylbenzoate (11.0 g, 48.0 mmol) and NBS (10.3 g, 57.6 mmol) in CCl4 (400 mL), and the resultant mixture was heated to reflux for 2 h. After cooling to room temperature, the mixture was diluted with hexanes (200 mL) before it was filtered and concentrated to give 14.7 g (crude yield 100%) of methyl 3-bromo-4-(bromomethyl)benzoate.

Workup

  1. temperatureto reflux for 2 h
  2. filtrationwas filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-015bef86c8f949a5869f22b00f04c875
Source dataset
uspto-grants-2002_05
Patent number
US06391901B1

Reaction notes

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