Preparation of substituted 3-aryl-5-haloalkyl-pyrazoles having herbicidal activity
AssigneeMonsanto Company
InventorsBruce C. Hamper, Michael K. Mao
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AssigneeMonsanto Company
InventorsBruce C. Hamper, Michael K. Mao
Estimating the term…
Processes for preparing substituted 3-aryl-5-haloalkyl-pyrazoles and, specifically, for preparing C.sub.1-5 alkyl esters of 5-[1-(C.sub.1-5 alkyl)-4-halo-5-(C.sub.1-3 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-fluor obenzoate, 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.
A process for preparing a compound of Formula IIId, ##STR110## comprising condensing a phenyl-diketone of Formula IIIb ##STR111## with hydrazine in a reaction mixture comprising a solvent for said phenyl-diketone to form an alkyl-pyrazole-precursor intermediate, hydrazine being present in the reaction mixture in a stoichiometric excess amount relative to the phenyl-diketone, the amount of excess hydrazine being at least about 15 mole percent of a reference amount, the reference amount being the sum of the molar amount of unreacted phenyl-diketone and the molar amount of intermediate formed,
A process for preparing a compound of Formula IIId, ##STR114## comprising condensing a phenyl-diketone of Formula IIIb ##STR115## with hydrazine in a reaction mixture comprising an organic solvent for said phenyl-diketone and water as a solvent for said hydrazine to form an alkyl-pyrazole-precursor intermediate, the reaction mixture having an organic phase and an aqueous phase, hydrazine being present in the reaction mixture in a stoichiometric excess amount relative to the phenyl-diketone,
Dependencies are inferred from the claim text.