Phenacyl bromide → 2-(3,5-Dichlorophenyl)oxirane

HRID 615885Notes

Reaction equation

HRID 615885 reaction equation
C(Br)C(C1C=CC=CC=1)=O.C1OC1C1C=CC=CC=1.[CH3:20][C:21]([C:23]1[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=1)=[O:22].CCOC(C)=O>C(Cl)(Cl)Cl>[Cl:30][C:25]1[CH:24]=[C:23]([CH:28]=[C:27]([Cl:29])[CH:26]=1)[CH:21]1[O:22][CH2:20]1

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 7276Styrene OxideHCID 8857Ethyl AcetateHCID 27580583',5'-Dichloroacetophenone

Product 1

HCID 134887952-(3,5-Dichlorophenyl)oxirane

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The phenacyl bromide intermediate for the above-mentioned styrene oxide is prepared by brominating 10 g of 3,5-dichloroacetophenone in 50 ml of CHCl3 /50 ml of EtOAc with 23.6 g of CuBr2. The mixture is heated at reflux for 2.5 hours and cooled to room temperature. After stirring for 16 hours at room temperature, the mixture is cooled in ice for 2 hours and filtered. The filter cake is washed with 50 ml of CHCl3 and the combined filtrates are twice decolorized with activated carbon, filtered, and evaporated to dryness in vacuo to afford the orange oil of the 3,5-dichlorostyrene oxide.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2.5 hours
  3. temperaturethe mixture is cooled in ice for 2 hours
  4. filtrationfiltered
  5. washThe filter cake is washed with 50 ml of CHCl3
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-4c4d8b7b34974a269754ad6c4534d5f7
Source dataset
uspto-grants-1985_02
Patent number
US04501751

Reaction notes

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