PROCESS FOR PREPARING 1-ALKYL-4- (2-CHLORO-3-ALKOXY-4-ALKYLSULFONYLBENZOYL) -5-HYDROXYPYRAZOLE AND RELATED COMPOUNDS

Herbicidal 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole compounds, as well as 1-halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene compounds and 2-chloro-3-alkoxy-4-alkylsulfonylbenzoic acid compounds, were prepared in good yield by the reaction of the corresponding 3-chloro com...

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Hauptverfasser: SIDDALL, THOMAS, LYMAN, KRUMEL, KARL, LEOPOLD, EDMONDS, MARK, VICTOR, MICHAEL, SCHOMAKER, JENNIFER, MARIE, ZETTLER, MARK, WENDEL, SHINKLE, SHARON, LOUISE, WEBSTER, JEFFERY, DALE
Format: Patent
Sprache:eng ; fre
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Zusammenfassung:Herbicidal 1-alkyl-4-(2-chloro-3-alkoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole compounds, as well as 1-halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene compounds and 2-chloro-3-alkoxy-4-alkylsulfonylbenzoic acid compounds, were prepared in good yield by the reaction of the corresponding 3-chloro compound with an alkali metal alkoxide compound. 1-Halo-2-chloro-3-alkoxy-4-alkylsulfonylbenzene and 1-halo-2,3-dichloro-4-alkylsulfonylbenzene compounds were converted to compounds having hydroxycarbonyl, alkoxycarbonyl, or 1-alkyl-5-hydroxypyrazole-4-carbonyl substituents in place of the 1-halo substituent by reaction with carbon monoxide and water, an alcohol, or a 1-alkyl-5-hydroxypyrazole compound, respectively, in the presence of a palladium II salt:trihydrocarbylphosphine complex type catalyst. La présente invention concerne des composés 1-alkyl-4-(2-chloro-3-alcoxy-4-alkylsulfonylbenzoyl)-5-hydroxypyrazole herbicides ainsi que des composés 1-halo-2-chloro-3-alcoxy-4-alkylsulfonylbenzène et des composés d'acide 2-chloro-3-alcoxy-4-alkylsulfonylbenzoïque, lesquels sont préparés avec un bon rendement par réaction du composé 3-chloro correspondant avec un composé alcoxyde alcalin. Les composés 1-halo-2-chloro-3-alcoxy-4-alkylsulfonylbenzène et 1-halo-2,3-dichloro-4-alkylsulfonylbenzène sont transformés en composés possédant des substituants hydroxycarbonyle, alcoxycarbonyle ou 1-alkyl-5-hydroxypyrazole-4-carbonyle à la place du substituant 1-halo par réaction avec l'oxyde de carbone et l'eau, un alcool, ou un composé 1-alkyl-5-hydroxy-pyrazole, respectivement, en présence d'un catalyseur du type complexe sel de palladium II:trihydrocarbylphosphine.