Benzoyl Peroxide → Methyl 5-(bromomethyl)-2-nitrobenzoate

HRID 591812Notes

Reaction equation

HRID 591812 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[C:8]([CH2:10][Br:15])[CH:7]=[CH:6][C:5]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3314122Methyl 5-methyl-2-nitrobenzoate

Product 1

HCID 13399988Methyl 5-(bromomethyl)-2-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

5-Methyl-2-nitrobenzoic acid methyl ester (27.1 g, 138.8 mmol) was dissolved in carbon tetrachloride (500 mL), and N-bromosuccinimide (29.6 g, 166.6 mmol) was added, followed by benzoyl peroxide (6.72 g, 27.7 mmol). The mixture was illuminated and gently refluxed for 4 hours. Then, the mixture was cooled and concentrated, then purified by column chromatography silica gel 230-400 mesh; 10% ethyl acetate in hexanes as eluent) to give 5-bromomethyl-2-nitrobenzoic acid methyl ester. Yield: 17.9 g (47%).

Workup

  1. customThe mixture was illuminated
  2. temperaturegently refluxed for 4 hours
  3. temperatureThen, the mixture was cooled
  4. concentrationconcentrated
  5. custompurified by column chromatography silica gel 230-400 mesh

Sources & evidence

ORD record
ord-c719a020c09d4c0e97eae8d74f3e09ee
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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