Benzoyl Peroxide → 2-Bromoethyl Benzoate

HRID 1613700

Reaction equation

HRID 1613700 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 solution of 120.14 g (0.80 mol) of 2-phenyl-1,3-dioxolane, 142.39 g (0.80 ml) of N-bromosuccinimide, 1 liter of carbon tetrachloride, and a catalytic amount of benzoyl peroxide was heated with stirring at reflux for 51/4 hours and cooled in accordance with the method disclosed in J. Org. Chem 43, 3418 (1978). The resulting mixture was filtered and the filtrate was concentrated and distilled. 147.8 g of product was collected; bp=104°-111° C./0.40 mm. (Rep. bp=90°-2° C./0.5 mm.)

Workup

  1. temperatureat reflux for 51/4 hours
  2. temperaturecooled in accordance with the method
  3. filtrationThe resulting mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. distillationdistilled
  6. custom147.8 g of product was collected

Sources & evidence

ORD record
ord-e7b1bbf959324c8394812b63d2803cc2
Source dataset
uspto-grants-1993_03
Patent number
US05194472

Linked notes

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