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

HRID 1786789

Reaction equation

HRID 1786789 reaction equation
[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]

Participants

3

Reactant 2

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

Product 1

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

Procedure

In order to produce gamma-cyhalothrin on an industrial scale it is desirable to find methods of making the final product that avoid the use of expensive reagents and have as few chemical stages as possible. The present invention provides a direct process to meet these requirements. There is therefore provided a process for the preparation of gamma-cyhalothrin (IV) comprising a) chlorinating 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid (I) to give 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride (II) and b) esterifying 1R cis-Z 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl cyclopropanecarboxylic acid chloride (II) with the (S)-cyanohydrin of 3-phenoxy benzaldehyde (III).

Workup

  1. customThe present invention provides a direct process
  2. customThere is therefore provided a process

Sources & evidence

ORD record
ord-f46c5fc8d12344fc8990e19beb9f3837
Source dataset
uspto-grants-2009_03
Patent number
US07507852B2

Linked notes

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