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

HRID 2427583Notes

Reaction equation

HRID 2427583 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[I: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]([I:11])=[CH:6][CH:7]=[CH:8][C:9]=1[CH2:10][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 23655277Methyl 2-iodo-6-methylbenzoate

Product 1

HCID 11268261Methyl 2-(bromomethyl)-6-iodobenzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 2-iodo-6-methyl-benzoic acid methyl ester (3.59 g, 13 mmol), N-bromosuccinamide (2.3 g, 13 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-iodo-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-eddb53b96fde42d4ad7b2021ae1cf61c
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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