Benzoyl Peroxide → 2-Propenoic acid, 3-[4-(bromomethyl)phenyl]-, ethyl ester

HRID 46983Notes

Reaction equation

HRID 46983 reaction equation
[CH3:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1.[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH:6]=[CH:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 334099Ethyl 3-(4-methylphenyl)-2-propenoate

Product 1

HCID 248203732-Propenoic acid, 3-[4-(bromomethyl)phenyl]-, ethyl esterYield 55%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl p-methylcinnamate (19.0 g., 0.1 mole), N-bromosuccinimide (19.6 g., 0.11 mole), benzoyl peroxide (200 mg.), and carbon tetrachloride is stirred and heated at reflux for 4 hours. The mixture is cooled and succinimide removed by filtration. The filtrate is washed with 5% sodium hydroxide solution, water, and brine, and dried over sodium sulfate. The solvent is removed at reduced pressure, and the residue is distilled in vacuo to yield 14.8 g. (55%) of the title compound, b.p. 137°-140° C. (0.1 mm.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 4 hours
  3. temperatureThe mixture is cooled
  4. customsuccinimide removed by filtration
  5. washThe filtrate is washed with 5% sodium hydroxide solution, water, and brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent is removed at reduced pressure
  8. distillationthe residue is distilled in vacuo
  9. customto yield 14.8 g

Sources & evidence

ORD record
ord-24f0dcb11e664cf49918f709983ab2a9
Source dataset
uspto-grants-1979_11
Patent number
US04175203

Reaction notes

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