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US 9,309,202 B2Granted
Method for producing 3,5-bis(fluoroalkyl)-pyrazol-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)-pyrazoles
AssigneeBayer CropScience AG
InventorsSergii Pazenok, Norbert Lui, Jean-Pierre Vors, Frederic R. Leroux, Florence Giornal
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Abstract
The present invention relates to novel 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and to a process for preparing 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)pyrazoles.
Claims13
Process for preparing 3,5-bis(fluoroalkyl)pyrazole of formula (Ia) and (Ib)
- in which
- R1 is selected from the group consisting of H, C1-12-alkyl, C3-8-cycloalkyl, C6-18-aryl, C7-19-arylalkyl or C7-19-alkylaryl, CH2CN, CH2CX3, CH2COOH, and CH2COOH—(C1-12)-alkyl, and
- X is independently F, Cl, Br, or I;
- R2 and R3 is each independently selected from C1-C6-haloalkyl groups;
- R4 is selected from the group consisting of H, Hal, COOH, (C═O)OR5, CN and (C═O)NR5R6, where R5 and R6 are each independently selected from the group consisting of C1-12-alkyl, C3-8-cycloalkyl, C6-18-aryl, C7-19-arylalkyl and C7-19-alkylaryl, or where R5 and R6 together with the nitrogen atom to which they are bonded may form a five- or six-membered ring;
- comprising
- in step A), reacting an α,α-dihaloamine of formula (II)
- in which X is Cl or F with a compound of formula (III)
- in which the R2 and R3 radicals are each as defined above and,
- in B), reacting the product thereof with a hydrazine of formula (IV)
- in which R1 is as defined above.
8 more elements
Compound of formula (Ia) or (Ib),
- wherein
- R1=H;
- R2═R3═CF2H and R4=COOEt.
Compound of formula (Ia) or (Ib),
- wherein
- R1=CH2COOEt;
- R2═R3═CF2H and R4=COOEt.
Compound of formula (VI)
- in which
- R2 and R3 are each independently selected from the group consisting of CF3, CF2H, and CF2Cl;
- R4 is selected from the group consisting of (C═O)OR5;
- R5 and R6 are each independently selected from the group consisting of C1-6-alkyl.
1 more element
Dependencies are inferred from the claim text.