Benzoyl Peroxide → Benzeneacetic acid, alpha-bromo-, methyl ester

HRID 1889173Notes

Reaction equation

HRID 1889173 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[Br:12]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:11])[CH:4]([Br:12])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 7559Methyl phenylacetateHCID 67184N-bromobutanimide

Product 1

HCID 137806Benzeneacetic acid, alpha-bromo-, methyl esterYield 107.5%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Phenyl-acetic acid methyl ester (10 gm, 66.6 mmol) was taken in carbon tetrachloride (100 ml). N-Bromosuccinimide (13.05 gm, 73.33 mmol) was added in one lot followed by benzoyl peroxide (1.77 gm, 7.3 mmol) and refluxed for 3 hours. The reaction mixture was cooled to room temperature and filtered; filtrate was washed with water followed by brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide bromo-phenyl-acetic acid methyl ester (16.4 gm) as a gummy mass.

Workup

  1. temperaturerefluxed for 3 hours
  2. filtrationfiltered
  3. washfiltrate was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ce06001093c4166ac89649443a10f10
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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