Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles...

C - Chemistry – Metallurgy – 07 – C

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C07C 49/80 (2006.01) C07C 45/45 (2006.01) C07C 51/373 (2006.01) C07C 51/62 (2006.01) C07C 65/32 (2006.01) C07C 67/343 (2006.01) C07C 69/738 (2006.01) C07C 69/76 (2006.01) C07D 231/10 (2006.01) C07D 231/12 (2006.01) C07D 231/16 (2006.01) C07F 9/6503 (2006.01)

Patent

CA 2258215

Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C1-5 alkyl esters of 5-[1-(C1-5 alkyl)-4-halo-5- (C1-3 haloalkyl)-1H-pyrazole-3-yl]-2,4-dihalo-benzoic acids such as isopropyl 5-[4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazole-3-yl]-2-chloro-4- fluorobenzoate, are presented. The described processes include novel approaches for forming phenyl-diketones, forming and alkylating pyrazoles, brominating heterocyclic compounds, oxidizing alkyl-substituted benzene compounds, and esterifying carboxylic acids. These processes may be combined to prepare 3-aryl-5-haloalkyl pyrazoles, or alternatively, used in subcombinations or individually to prepare intermediates or other useful compounds.

L'invention concerne des procédés de préparation de 3-aryle-5-haloalkyle-pyrazoles substitués, et spécifiquement de préparation d'esters alcoyliques C¿1-5? d'acides 5-[1-(alkyle C¿1-5?)-4-halo-5-(haloalkyle C¿1-3?)-1H-pyrazole-3-yl]-2,4-dihalo-benzoïques tels que isopropyl 5-[4-bromo-1-méthyl-5-(trifluorométhyl)-1H-pyrazole-3-yl]-2-chloro-4-fluorobenzoate. Les procédés décrits comprennent de nouvelles approches de formation de phényl-dicétones, de formation et d'alkylation de pyrazoles, de bromation de composés hétérocycliques, d'oxydation de composés benzéniques à substitution alkyle, et d'estérification d'acides carboxyliques. On peut combiner ces procédés afin de préparer des 3-aryle-5-haloalkyle pyrazoles ou alternativement les utiliser dans des sous-combinaisons ou individuellement pour préparer des intermédiaires ou d'autres composés utiles.

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