Azobisisobutyronitrile → Methyl 2-(bromomethyl)-4-nitrobenzoate

HRID 2280334Notes

Reaction equation

HRID 2280334 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH3:13].C1C(=O)N([Br:22])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13][Br:22]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 15088700Methyl 2-methyl-4-nitrobenzoate

Product 1

HCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoateYield 92.4%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-Methyl-4-nitro-benzoic acid methyl ester (3.08 g, 15.79 mmole) in 125 ml carbontetrachloride was added NBS (3.1 g, 17.38 mmole) and AIBN (390 mg, 2.38 mmole). The reaction mixture was heated at reflux under light for 22 hours. The reaction mixture was cooled down, concentrated to half, filtered off, solid was washed with 25 ml carbontetrachloride. The filtrate was concentrated to give 4 g crude product, containing about 20% unreacted starting material. This was used for next step without purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under light for 22 hours
  3. temperatureThe reaction mixture was cooled down
  4. concentrationconcentrated to half
  5. filtrationfiltered off
  6. washsolid was washed with 25 ml carbontetrachloride
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8793d73f8cbf48f5ae47fd9e4f6a9f82
Source dataset
uspto-grants-2015_09
Patent number
US09138427B2

Reaction notes

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