Ethyl 2-bromo-2-cyanoacetate → Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate

HRID 894486

반응식

HRID 894486 반응식
[Cl:1][C:2]([Cl:8])=[CH:3][CH:4]=[C:5]([CH3:7])[CH3:6].[CH2:9]([O:11][C:12](=[O:17])[CH:13](Br)[C:14]#[N:15])[CH3:10]>[Cu]>[CH2:9]([O:11][C:12]([C:13]1([C:14]#[N:15])[CH:4]([CH:3]=[C:2]([Cl:8])[Cl:1])[C:5]1([CH3:7])[CH3:6])=[O:17])[CH3:10]

참가 물질

4

반응물 2

HCID 14469Ethyl 2-bromo-2-cyanoacetateHCID 1087461,3-Pentadiene, 1,1-dichloro-4-methyl-

생성물 1

HCID 12898169Ethyl 1-cyano-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate

시약·촉매·용매 1

HCID 23978Copper촉매

실험 절차

A mixture of 1,1-dichloro-4-methylpenta-1,3-diene (15.1 parts) ethylbromocyanoacetate (19.2 parts), copper-containing catalyst (as indicated in the table below), acid binder (as indicated in the table below) in solvent (as indicated in the table below; 100 parts by volume) is heated to the reflux temperature of the mixture if below 90° C., otherwise at a temperature not exceeding 90° C., and held at the reaction temperature for 6 hours. After removal of the solvent by distillation under reduced pressure the residue is extracted with a mixture of toluene (100 parts by volume), water (150 parts) and concentrated hydrochloric acid (100 parts by volume). The extract is filtered, the toluene layer is separated, washed with water (4×50 parts) and the crude ethyl-1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate is isolated by distilling off the toluene under reduced pressure. The yield, strength and composition of the product obtained is given in the table below together with other reaction details.

후처리

  1. additioncontaining catalyst (
  2. temperature100 parts by volume) is heated to the reflux temperature of the mixture if below 90° C., otherwise at a temperature not
  3. customexceeding 90° C.
  4. customAfter removal of the solvent
  5. distillationby distillation under reduced pressure the residue
  6. extractionis extracted with a mixture of toluene (100 parts by volume), water (150 parts) and concentrated hydrochloric acid (100 parts by volume)
  7. filtrationThe extract is filtered
  8. customthe toluene layer is separated
  9. washwashed with water (4×50 parts)

출처 및 근거

ORD 기록
ord-63c8d51ddccc40f49691c52381e16091
출처 데이터셋
uspto-grants-1981_08
특허 번호
US04284582

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