Patent ID: 8299260

Claim:
A process for preparing an aryl-substituted pyrazole of general formula (I) in which R 1 is hydroxyl, alkoxy, aryloxy or halogen, R 2 is hydroxyl, alkoxy, arylalkoxy, alkylthio, halogen, O—(C═O)alkyl, O—(C═O)O-alkyl, (C═O)haloalkyl, OSO 2 alkyl, OSO 2 -haloalkyl or OSO 2 -aryl, R 3 is halogen, CN, NO 2 , alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or cycloalkylamino, Z is CH or N, characterized in that (A) an alkoxyenone or an enaminoketone of formula (II) in which R 4 is H, alkyl, arylalkyl, —(C═O)alkyl, (C═O)haloalkyl, —(C═O)O-alkyl, SO 2 alkyl, SO 2 -haloalkyl or SO 2 -aryl, X is, chlorine, bromine or iodine, R 5 is alkoxy, dialkylamino, cycloalkylamino or thioalkyl, or is cycloalkyl which may optionally contain 1-3 heteroatoms from the group of O, N or S, is reacted with an arylhydrazine of the formula (III) in which R 3 is halogen, CN, NO 2 , alkyl, cycloalkyl, haloalkyl, halocycloalkyl, alkoxy, haloalkoxy, alkylamino, dialkylamino or cycloalkylamino, Z is CH or N, to give a 1-aryl-substituted dihydro-1H-pyrazole of the formula (IV) in which X, R 3 , R 4 and Z are each as defined above, (B) the latter is optionally converted further, without preceding isolation, with elimination of water, to a 1-aryl-substituted trihalomethylpyrazole of the formula (V) in which X, R 3 , R 4 and Z are each as defined above, (C) the compound of the general formula (V) is converted with addition of HC1, H 2 SO 4 or a base, to a pyrazolecarboxylic acid of the formula (VI) in which R 3 , R 4 and Z are each as defined above, (D) the latter is converted, after detaching the R 4 group, to a hydroxymethylpyrazole acid of the formula (VII) in which R 3 and Z are as defined above, and (E) the latter is converted to a compound of the formula (I)