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

HRID 894494

Reaction equation

HRID 894494 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].[Cl:9][C:10]([Cl:18])=[CH:11][CH:12](Br)[C:13](Br)([CH3:15])[CH3:14].C(=O)([O-])[O-].[Ca+2]>C(O)C.[Cl-].[Ca+2].[Cl-].[Cu]>[C:6]([C:5]1([C:4]([O:3][CH2:1][CH3:2])=[O:8])[CH:12]([CH:11]=[C:10]([Cl:18])[Cl:9])[C:13]1([CH3:15])[CH3:14])#[N:7]

Participants

7

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 10112Calcium CarbonateHCID 205742811,1-Dichloro-3,4-dibromo-4-methylpent-1-ene

Product 1

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

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 5284359Calcium ChlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethylcyanoacetate, 1,1-dichloro-3,4-dibromo-4-methylpent-1-ene and calcium carbonate is heated in ethanol (100 parts by volume) at reflux in the presence of calcium chloride (22.2 parts) and copper salt as catalyst. The crude ethyl 1-cyano-3-(2',2'-dichlorovinyl)-2,2-dimethylcyclopropane-1-carboxylate is isolated as described in Example 77. Details are given in the following table:

Sources & evidence

ORD record
ord-b83bdd34c25d451badfaded055888d16
Source dataset
uspto-grants-1981_08
Patent number
US04284582

Linked notes

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