Azobisisobutyronitrile → Methyl 2-bromo-6-(bromomethyl)benzoate

HRID 2251840Notes

Reaction equation

HRID 2251840 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Br:11].C1C(=O)N([Br:20])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:12])[C:4]1[C:9]([CH2:10][Br:20])=[CH:8][CH:7]=[CH:6][C:5]=1[Br:11]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 11564857Methyl 2-bromo-6-methylbenzoate

Product 1

HCID 23574705Methyl 2-bromo-6-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Bromo-6-methyl-benzoic acid methyl ester (2.18 g), NBS (4.89 g), and AIBN (0.486 g) were taken into CCl4 (15 mL) and heated at reflux for 8 h. After cooling to RT, the solid was removed by filtration, and the filtrate was concentrated to give an orange oil as crude material. Purification by chromatography (silica gel, 100 g, 5-15% EtOAc/hexanes) afforded 2-bromo-6-bromomethyl-benzoic acid methyl ester as colorless oil.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 h
  3. customthe solid was removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customto give an orange oil as crude material
  6. customPurification by chromatography (silica gel, 100 g, 5-15% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a195cb00f2214f9bb863572157f02241
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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