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ChemicalBook CAS DataBase List Fluoxapiprolin
1360819-11-9

Fluoxapiprolin synthesis

2synthesis methods
Fluoxapiprolin is produced through a multi-step industrial synthesis typical of modern piperidinyl-amide fungicides, combining tightly controlled heterocycle construction with late stage functionalisation to achieve the molecule’s distinctive diaryl-substituted piperidine core. Commercial routes begin with preparation of the substituted piperidine scaffold, usually via catalytic hydrogenation or reductive amination of a protected precursor, followed by introduction of the difluoro- and chloro-substituted aromatic rings through sequential coupling reactions under anhydrous, high-purity conditions. The amide linkage is then formed by reacting the activated carboxylic acid derivative with the piperidinyl intermediate, often using carbodiimide or mixed-anhydride chemistry optimised for scale.
Ethanone, 2-chloro-1-[5-[2-chloro-6-[(methylsulfonyl)oxy]phenyl]-4,5-dihydro-3-isoxazolyl]-

1446134-16-2
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Fluoxapiprolin

1360819-11-9
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Yield:-

Steps:

Multi-step reaction with 3 steps
1.1: hydrogenchloride / ethanol; water / 4 h / 70 °C
2.1: tributyl-amine / tetrahydrofuran / 0.25 h / 45 °C
2.2: 2.5 h / 45 °C
3.1: sodium carbonate; tetrabutylammomium bromide / acetonitrile / 3.5 h / 70 °C

References:

WO2015/181097,2015,A1

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