Patent ID: 8350053

Claim:
A process for preparing 1-alkyl-3-haloalkylpyrazole-4-carboxylic acid derivatives of the formula (I) in which: R 1 is selected from the group consisting of C 1-12 -alkyl, C 3-8 -cycloalkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, C 6-8 -aryl, C 7-19 -arylalkyl and C 7 -19 -alkylaryl groups, each of which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —(C═O)R′, —CN and —CONR 2 ′, where R′ is hydrogen or a C 1-12 -alkyl group; R 2 is selected from C 1 -C 4 -alkyl groups which may be substituted by one, two or three halogen atoms selected from the group consisting of F, Cl and Br or by a CF 3 group; Y is selected from the group consisting of (C═O)OR 3 , CN and (C═O)NR 4 R 5 , where R 3 , R 4 and R 5 independently of one another are selected from the group consisting of hydrogen, C 1-12 -alkyl, C 3-8 -cycloalkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, C 6-8 -aryl, C 7-19 -arylalkyl and C 7-19 -alkylaryl groups, each of which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —SiR′ 3 , —COOR′, —(C═O)R′, —CN and —CONR 2 ′, where R′ is hydrogen or a C 1-12 -alkyl group; or where R 4 and R 5 together with the nitrogen atom to which they are attached may form a 5- or 6-membered ring; comprising reacting a 2-acylated acrylic acid derivative of the formula (II), in which: Z 1 and Z 2 independently of one another are selected from the group consisting of O and S; R 6 is selected from the group consisting of C 1-12 -alkyl, C 3-8 -cycloalkyl, C 2-12 -alkenyl, C 2-12 -alkynyl, C 6-8 -aryl, C 7-19 -arylalkyl and C 7-19 -alkylaryl groups, each of which may be substituted by one or more groups selected from the group consisting of —R′, —X, —OR′, —SR′, —NR′ 2 , —COOR′, —(C═O)R′, —CN and —CONR 2 ′, where R′ is hydrogen or a C 1-12 -alkyl group; R 2 and Y have the meanings described above; with an N-alkylhydrazine of the formula (III) in which: R 1 has the meaning described above; in the presence of a compound of the formula (IV) in which: R 7 , R 8 independently of one another are selected from the group consisting of H, C 1-12 -alkyl, C 3-8 -cycloalkyl, C 6-18 -aryl, C 7-19 -arylalkyl or C 7-19 -alkylaryl radicals; M is selected from the group consisting of O, S, Se, NH, and NR′, where R′ has the meanings defined above.