Benzoyl Peroxide → 2-Bromomethyl-3-chloro-benzoic acid methyl ester

HRID 915355Notes

Reaction equation

HRID 915355 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH3:11].[Br:13]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:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[CH2:11][Br:13]

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 5077673Methyl 3-chloro-2-methylbenzoate

Product 1

HCID 110327262-Bromomethyl-3-chloro-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a suspension of 3-chloro-2-methylbenzoic acid methyl ester (5.62 g, 30.4 mmol), and N-bromosuccinimide (5.94 g, 33.4 mmol) in carbon tetrachloride (200 mL) was added benzoyl peroxide (800 mg, 3.30 mmol). The resulting suspension was immersed in an oil bath held at 85° C., and illuminated with a 300W halogen worklight. After stirring for 16 hours with heat and illumination the reaction mixture was allowed to cool to ambient temperature, filtered to remove the insoluble succinimide, and concentrated under reduced pressure to afford 2-bromomethyl-3-chlorobenzoic acid methyl ester as a yellow semi-solid. This crude material was carried on to the next step without purification.

Workup

  1. customThe resulting suspension was immersed in an oil bath
  2. customheld at 85° C.
  3. temperaturewith heat
  4. filtrationfiltered
  5. customto remove the insoluble succinimide
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3b56bee1961144b4aa3ff7812de85e48
Source dataset
uspto-grants-2007_09
Patent number
US07265131B2

Reaction notes

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