Benzoyl Peroxide → Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

HRID 2427645Notes

Reaction equation

HRID 2427645 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[Cl:12].[Br:14]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:13])[C:4]1[C:5]([Cl:12])=[CH:6][C:7]([Br:11])=[CH:8][C:9]=1[CH2:10][Br:14]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 45480505Methyl 4-bromo-2-chloro-6-methylbenzoate

Product 1

HCID 59512234Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-bromo-2-chloro-6-methyl-benzoic acid methyl ester (2.447 g, 9.27 mmol,), N-bromosuccinimide (1.815 g, 10.2 mmol), and benzoyl peroxide (0.051 g, 0.22 mmol) in carbon tetrachloride (30 mL) was refluxed until most of the starting materials were consumed (as analyzed by GC/MS). The resulting mixture was filtered and the filtrate concentrated to afford 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester. The product was used without further purification.

Workup

  1. temperaturewas refluxed until most of the starting materials
  2. customwere consumed (as analyzed by GC/MS)
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-3cfd6acd75324c6e98fe2e700e3d8aa4
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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