Benzoyl Peroxide → 2-Bromoethyl Benzoate

HRID 248789

Reaction equation

HRID 248789 reaction equation
[C:1]1([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:12]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:7]([O:11][CH2:10][CH2:9][Br:12])(=[O:8])[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 702932-Phenyl-1,3-dioxolane

Product 1

HCID 5230902-Bromoethyl Benzoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 120.14 grams (0.80 mol) of 2-phenyl-1,3-dioxolane, 142.39 grams (0.80 mol) of N-bromosuccinimide, 1 liter of carbon tetrachloride and a catalytic amount of benzoyl peroxide was heated with stirring at reflux for 5.25 hours and then cooled. The mixture was filtered, and the filtrate was concentrated to an oil. Distillation of this oil gave 147.8 grams; (80.65% of theory) of the product; bp=104°-111° C./0.40 mm.

Workup

  1. temperatureat reflux for 5.25 hours
  2. temperaturecooled
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated to an oil
  5. distillationDistillation of this oil
  6. customgave 147.8 grams

Sources & evidence

ORD record
ord-1044f04a15c24fb09d0e70d2d8fc00f4
Source dataset
uspto-grants-1993_05
Patent number
US05212035

Linked notes

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