1,2-Dichloroethane → 2-Chlorovinyl 2,4-dichloro5-fluoro-phenyl ketone

HRID 2231356Notes

Reaction equation

HRID 2231356 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].[Cl-].[Al+3].[Cl-].[Cl-].[Cl:17][CH2:18][CH2:19]Cl.C#C>C(Cl)Cl>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([CH:19]=[CH:18][Cl:17])=[O:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6326AcetyleneHCID 27368212,4-Dichloro-5-fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 542986662-Chlorovinyl 2,4-dichloro5-fluoro-phenyl ketone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

113.75 g (0.5 mole) of 2,4-dichloro-5-fluorobenzoyl chloride are added dropwise to a suspension of 73 g of anhydrous aluminum chloride and 200 ml of dry 1,2-dichloroethane at 0°-10° C., while cooling with ice and stirring. Acetylene is passed in at 40°-50° C. for 6.5 hours. The reaction mixture is poured onto ice, the organic phase is taken up in methylene chloride and the mixture is subsequently extracted with methylene chloride. After drying with sodium sulphate, the solvent is distilled off in vacuo. 121.7 g of 2-chlorovinyl 2,4-dichloro-5-fluoro-phenyl ketone are obtained as a crude product of melting point 65°-70° C. Distillation under a fine vacuum gives 99.8 g (78.7%) of pure product of boiling point: 124°-128° C./0.1 mbar and melting point 71°-73° C.

Workup

  1. temperaturewhile cooling with ice
  2. additionThe reaction mixture is poured onto ice
  3. extractionthe mixture is subsequently extracted with methylene chloride
  4. dry with materialAfter drying with sodium sulphate
  5. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-32d6bbfe61a84b47b5801036de69a776
Source dataset
uspto-grants-1988_11
Patent number
US04782156

Reaction notes

Loading…