60066-84-4

Usage

InChI:InChI=1/C10H15Cl3O2/c1-4-15-8(14)7-6(9(7,2)3)5-10(11,12)13/h6-7H,4-5H2,1-3H3/t6-,7+/m1/s1

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 61446-87-5 1,1,1-trichloro-4-methyl-pent-3-ene 
• 60066-53-7 ethyl 4,6,6,6-tetrachloro-3,3-dimethylhexanoate 
• 64-17-5 ethanol 
• 60066-54-8 ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate 

Downstream Products

• 63142-57-4 ethyl (+/-)-trans-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 63142-56-3 ethyl (+/-)-cis-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 
• 63406-19-9 ethyl cis-2-(2-chlorethynyl)-3,3-dimethylcyclopropanecarboxylate 
• 55701-05-8 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 59609-49-3 ethyl 3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate 

Relevant academic research and scientific papers

A Practical and Efficient Synthesis of Fluorinated Pyrethroids. cis-3-(2-Chloro--3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylates

A practical and efficient route to fluorinated pyrethroids has been developed which involves the selective formation of the cis-cyclopropane ring using intramolecular alkylation of the haloaldehyde and a novel transformation of the aldehydes to the corresponding esters via the cyanohydrins.

A Convenient Synthesis of Ethyl 3-(2,2-Dihaloethenyl)-2,2-dimethylcyclopropanecarboxylates and Its Modifications for cis-Isomer Enrichment

A synthesis of the title compounds 5 involves the reaction between 3-methyl-2-buten-1-ol and triethyl orthoacetate to produce ethyl 3,3-dimethyl-4-pentenoate, which is followed by the addition of various carbon tetrahalides to the double bond.The reaction of resulting adducts with a base affords 5 in high yields.Stereoselective preparation of the cis-isomer was achieved by the following two methods: First one involves selective transformation of ethyl 4-bromo-6,6,6-trichloro-3,3-dimethylhexanoate to ethyl 6,6,6-trichloro-2,3-dimethyl-4-hexanoate (8a) with piperidine followed by the selective conversion of 8a to cis-2,2-dichloroethenyl compound (cis-5a).Second one is based on the stereoselective cyclization of ethyl 4,6,6,6-tetrachloro-3,3-dimethyl-hexanoate (t-BuONa/solvent/HMPA) to ethyl cis-2,2-dimethyl-3-(2,2,2-trichloroethyl)cyclopropanecarboxylate which is transformed into cis-5a without cis-trans isomerisation.

Chiral copper complex

A chiral copper complex which is produced by the reaction of a chiral copper complex of the formula: STR1 wherein R1 is (a) alkyl group, or (b) aralkyl group; R2 is (a) 2-alkoxyphenyl group, or (b) 2-alkoxy-5-alkylphenyl group; either one of X1 and X2 is (a) hydrogen atom, (b) halogen atom (c) alkyl group, (d) alkoxy group, or (e) nitro group, or adjecent X1 and X2 together form a benzo group, with a mono-substituted hydrazine of a formula: wherein R3 is (a) aryl group, (b) aralkyl group, or (c) alkyl group. The copper complex is used as a catalyst in the production of an optically active alkyl cyclopropanecarboxylate.

ASYMMETRIC SYNTHESIS OF PERMETHRIC ACID. STEREOCHEMISTRY OF CHIRAL COPPER CARBENOID REACTION.

The most effective optical isomer (1R-cis) of permethric acid (2, R=H), a potent intermediate in the production of synthetic pyrethroid, was enantioselectively prepared.

Process for preparing dihalovinylcyclopropanecarboxylates

Novel syntheses of dihalovinylcyclopropanecarboxylates, including potent insecticides, are described. The processes begin with the reaction between an alkenol and an orthoester to produce a γ-unsaturated carboxylate, followed by the catalyzed addition of a carbon tetrahalide to the double bond and dehydrohalogenation to produce a cyclopropane derivative.