Hydrochloric Acid → 2,2-Dichlorovinyl 2,4-dichloro-5-fluorophenyl ketone

HRID 64978

反応式

HRID 64978 の反応式
[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:13][C:14]([Cl:16])=[CH2:15].[Cl-].[Al+3].[Cl-].[Cl-].Cl>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:15]=[C:14]([Cl:16])[Cl:13])=[O:5]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 6366Vinylidene chlorideHCID 27368212,4-Dichloro-5-fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 136450062,2-Dichlorovinyl 2,4-dichloro-5-fluorophenyl ketone収率 96.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

136.5 g (0.6 mole) of 2,4-dichloro-5-fluorobenzoyl chloride and 97 g (1 mole) of 1,1-dichloroethylene are successively added dropwise to a suspension of 84 g of anhydrous aluminum chloride in 300 ml of methylene chloride, while cooling with ice and stirring, during which the temperature should not exceed 30° C. The mixture is stirred at room temperature for 3 hours and poured onto a mixture of about 600 g of ice and 60 ml of concentrated hydrochloric acid, the organic phase is separated off and the aqueous phase is subsequently extracted three times with 100 ml of methylene chloride. The methylene chloride solution is washed with 100 ml of water and dried with sodium sulphate and the solvent is distilled off in vacuo. The residue (218.8 g) is heated at 130°-140° C. with 0.34 g of triphenylphosphine until the initially vigorous evolution of HCl has ended (about 3/4 hour). Distillation under a fine vacuum gives 167.1 g (96.4%) of 2,2-dichlorovinyl 2,4-dichloro-5-fluorophenyl ketone of boiling point 121°-123° C./0.13 mbar, melting point 64°-65° C.

後処理

  1. temperaturewhile cooling with ice
  2. customexceed 30° C
  3. stirringThe mixture is stirred at room temperature for 3 hours
  4. customthe organic phase is separated off
  5. extractionthe aqueous phase is subsequently extracted three times with 100 ml of methylene chloride
  6. washThe methylene chloride solution is washed with 100 ml of water
  7. dry with materialdried with sodium sulphate
  8. distillationthe solvent is distilled off in vacuo
  9. temperatureThe residue (218.8 g) is heated at 130°-140° C. with 0.34 g of triphenylphosphine until the initially vigorous evolution of HCl
  10. custom(about 3/4 hour)
  11. distillationDistillation under a fine vacuum

出典と根拠

ORDレコード
ord-03763ae0925344f3812ce949ad967c38
出典データセット
uspto-grants-1986_09
特許番号
US04611080

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