Benzoyl Peroxide → Ethyl 3-(3-Bromo-1-propenyl)benzoate

HRID 26614Notes

Reaction equation

HRID 26614 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:2][CH3:3].[Br:15]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.BrCC=CC1C=C(C=CC=1)C([O-])=O>C(Cl)(Cl)(Cl)Cl>[Br:15][CH2:3][CH:2]=[CH:1][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

6

Reactant 4

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 53648757Ethyl 3-(1-propenyl)benzoateHCID 73677479HCID 73677479, compound

Product 1

HCID 54195232Ethyl 3-(3-Bromo-1-propenyl)benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of ethyl 3-(1-propenyl)benzoate (14.0 g., 0.074 mole), N-bromosuccinimide (14.9 g., 0.084 mole), benzoyl peroxide (150 mg.), and carbon tetrachloride (75 ml.) is stirred and heated at reflux for 46 hours. The mixture is cooled. Solids are filtered off and the filtrate is washed with water and dried over magnesium sulfate. The solvent is evaporated and the residual oil distilled to yield 10.2 g. (51%) of ethyl (3-(3-bromo-1-propenyl)benzoate, b.p. 129°-131° C. (0.05 mm.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 46 hours
  3. temperatureThe mixture is cooled
  4. filtrationSolids are filtered off
  5. washthe filtrate is washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is evaporated
  8. distillationthe residual oil distilled
  9. customto yield 10.2 g

Sources & evidence

ORD record
ord-ba3d22d0385542d49190f1138c7c4221
Source dataset
uspto-grants-1979_04
Patent number
US04150235

Reaction notes

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