Benzoyl Peroxide → Ethyl 2-(bromomethyl)-4-nitrobenzoate

HRID 390410Notes

Reaction equation

HRID 390410 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH3:14])[CH3:2].[Br:16]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[CH2:14][Br:16])[CH3:2]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 21345698Ethyl 2-Methyl-4-nitrobenzoate

Product 1

HCID 58066683Ethyl 2-(bromomethyl)-4-nitrobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

2-Methyl-4-nitro-benzoic acid ethyl ester (6.0 g, 28.7 mmol), N-bromosuccinimide (5.4 g, 30.3 mmol), and benzoyl peroxide (0.695 g, 2.87 mmol) were combined in CCl4 (250 mL). The reaction was heated to reflux and stirred under a halogen lamp overnight. After aqueous work-up, the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. customAfter aqueous work-up, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-f7a31bdb66ee4db6859c9b4543a86016
Source dataset
uspto-grants-2013_02
Patent number
US08383654B2

Reaction notes

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