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

HRID 1248147Notes

Reaction equation

HRID 1248147 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-7318cea39b5e4520a58c219b17565a7b
Source dataset
uspto-grants-1985_06
Patent number
US04522822

Reaction notes

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