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

HRID 2427582Notes

Reaction equation

HRID 2427582 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:5]=1[Cl:11].[Br:13]NC(=O)CCC(N)=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:12])[C:4]1[C:5]([Cl:11])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 22935202Methyl 2-chloro-6-methylbenzoate

Product 1

HCID 22935208Methyl 2-(bromomethyl)-6-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-chloro-6-methyl-benzoic acid methyl ester (1.84 g, 10 mmol), N-bromosuccinamide (1.95 g, 11 mmol), and benzoyl peroxide (0.056 g, 0.21 mmol) in carbon tetrachloride (20 mL) was heated at reflux until the starting materials were mostly consumed. Workup afforded 2-bromomethyl-6-chloro-benzoic acid methyl ester. The material was used without further purification.

Workup

  1. temperaturewas heated
  2. temperatureat reflux until the starting materials
  3. customwere mostly consumed

Sources & evidence

ORD record
ord-5e05d5e9d590497e8014c6a17e2f4653
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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