Benzoyl Peroxide → Ethyl 3-bromo-4-(bromomethyl)benzoate

HRID 2970

Reaction equation

HRID 2970 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].C1C(=O)N([Br:21])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH2:13][Br:21])[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 14945865Ethyl 3-bromo-4-methylbenzoate

Product 1

HCID 13877460Ethyl 3-bromo-4-(bromomethyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1.0 mmol of ethyl 3-bromo-4-methylbenzoate, 1.0 mmol NBS, and 0.02 mmol benzoyl peroxide in 5 mL CCl4 was refluxed for 4 h and then processed by filtration and chromatography to provide ethyl 3-bromo-4-bromomethylbenzoate as an oil.

Workup

  1. temperaturewas refluxed for 4 h
  2. filtrationprocessed by filtration and chromatography

Sources & evidence

ORD record
ord-43fc139c41d84237a967f7fa62214d1c
Source dataset
uspto-grants-1998_03
Patent number
US05731432

Linked notes

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