Benzoyl Peroxide → Methyl 2-(bromomethyl)-3-nitrobenzoate

HRID 420613Notes

Reaction equation

HRID 420613 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH3:13].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1(=O)NC(=O)CC1>C(Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][Br:15]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 11439SuccinimideHCID 67184N-bromobutanimideHCID 601165Methyl 2-methyl-3-nitrobenzoate

Product 1

HCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

25.55 g (130.9 mmol) of 2-methyl-3-nitrobenzoic acid methyl ester is added to 300 ml of carbon tetrachloride, and mixed with 25.6 g (141.7 mmol) of N-bromosuccinimide and 62.8 mg of benzoyl peroxide. After seven days of refluxing, the succinimide is suctioned off after cooling, and then the filtrate is spun in until a dry state is reached. The desired compound that is incorporated in crude form into the next stage remains.

Workup

  1. temperatureAfter seven days of refluxing
  2. temperatureafter cooling

Sources & evidence

ORD record
ord-bac3f96a75ac43479751c769eee1363d
Source dataset
uspto-grants-2012_01
Patent number
US08097627B2

Reaction notes

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