gamma-Cyhalothrin → (1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride

HRID 2377124

Reaktionsgleichung

Reaktionsgleichung von HRID 2377124
[CH3:1][C:2]1([CH3:31])[C@H:4]([C:5](O[C@@H](C2C=CC=C(OC3C=CC=CC=3)C=2)C#N)=[O:6])[C@@H:3]1/[CH:24]=[C:25](\[Cl:30])/[C:26]([F:29])([F:28])[F:27].[Cl:32]/C(/C(F)(F)F)=C\[C@@H]1[C@H](C(O)=O)C1(C)C>>[Cl:30]/[C:25](/[C:26]([F:29])([F:28])[F:27])=[CH:24]\[C@@H:3]1[C@H:4]([C:5]([Cl:32])=[O:6])[C:2]1([CH3:31])[CH3:1]

Komponenten

3

Edukt 2

HCID 6440554gamma-CyhalothrinHCID 11184106(1S-cis)-Cyhalothric acid

Produkt 1

HCID 11334477(1RS)-cis-3-(Z-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride

Versuchsvorschrift

There is therefore provided a process for the preparation of gamma-cyhalothrin comprising a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid (V) to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride (III); b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride (III) with 3-phenoxy benzaldehyde (IV) in the presence of a source of cyanide to form a diastereoisomeric mixture of 1R cyhalothrin isomers (II) and c) epimerising the diastereoisomeric mixture (II) under conditions in which the least soluble diastereoisomer (I) crystallises from solution.

Aufarbeitung

  1. customThere is therefore provided a process

Quellen und Nachweise

ORD-Eintrag
ord-2ab09f6ef2cc4478b00bcda7502ad4b2
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468453B2

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