Benzoyl Peroxide → 2-Bromomethyl-4-fluoro-6-cyano-benzoic acid methyl ester

HRID 2427754Notes

Reaction equation

HRID 2427754 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[C:9]([CH3:10])=[CH:8][C:7]([F:11])=[CH:6][C:5]=1[C:12]#[N:13].[Br:15]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:14])[C:4]1[C:5]([C:12]#[N:13])=[CH:6][C:7]([F:11])=[CH:8][C:9]=1[CH2:10][Br:15]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 9834204N-BromosuccinamideHCID 57949316Methyl 2-cyano-4-fluoro-6-methylbenzoate

Product 1

HCID 579494872-Bromomethyl-4-fluoro-6-cyano-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 4-fluoro-2-cyano-6-methyl-benzoic acid methyl ester (1.04 g, 5.38 mmol), N-bromosuccinamide (1.25 g, 7.0 mmol), and benzoyl peroxide (0.024 g, 0.146 mmol) in carbon tetrachloride (50 mL) was heated at reflux until majority of ester was consumed (as analyzed by GC/MS). The resulting mixture was filtered, the filtrate was concentrated to afford 2-bromomethyl-4-fluoro-6-cyano-benzoic acid methyl ester. The material was used without further purification.

Workup

  1. temperaturewas heated
  2. customwas consumed (as analyzed by GC/MS)
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-7502ff36b518492ebb3b2e76c5237736
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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