Basf Se Corporation

Basf Aktiengesellschaft

Sebastian Peer Smidt

Michael Keil

Michael Rack

Thomas Zierke

Volker Maywald

Bernd Wolf

Christopher Koradin

Jochen Dietz

Thomas Grote

Joachim Rheinheimer

Jan Klaas Lohmann

Ansgar Gereon Altenhoff

Joachim Schmidt-Leithoff

Heidi Emilia Saxell

Martin Sukopp

Cedric Dieleman

Wolfgang Reichert

Sandra Löhr

Kathrin Wissel-Stoll

Nina Challand

Markus Nett

Manuel Budich

Chistopher Koradin

The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters, 2-(aminomethylidene)-4,4-difluoro-3-oxobutteric esters of the formula (I) in which R, Rand Rindependently of one another are C-C-alkyl, C-C-haloalkyl, C-C-alkenyl, C-C-cycloalkyl or benzyl or NRRis a 5- to 10-membered heterocyclic radical, to a process for preparing compounds of the formula (I) wherein an appropriate 3-aminoacrylic ester is reacted with difluoroacetyl fluoride and to the use of compounds of the formula (I) in the process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.

Process for preparing 2-(aminomethylidene)-4,4-difluoro-3-oxobutyric esters

The present invention relates to a process for preparing 2-(aminomethylidene)-4,4-dihalo-3-oxobutyric esters of the formula (I), wherein R, R, Rare C-C-alkyl, C-C-haloalkyl, C-C-alkenyl, C-C-cycloalkyl or benzyl, and/or Rtogether with Rand the nitrogen atom to which the two radicals are attached are a heterocyclic radical, in which a corresponding 3-aminoacrylic ester is reacted with a halogen-substituted acetyl fluoride in the presence of at least one alkali or alkaline earth metal fluoride; and the further conversion of halogen-substituted 2-(aminomethylidene)-3-oxobutyric esters of the formula (I) to halomethyl-substituted pyrazol-4-ylcarboxylic acids and their esters.

Method for the production of halogen-substituted 2-(aminomethylidene)-3-oxobutyric acid esters

The present invention relates to a process for preparing 2-aminobiphenyls of the formula I in which The invention also relates to a process for preparing pyrazolecarboxamides of such 2-aminobiphenyls.

Method for producing 2-aminobiphenylene

A process for preparing substituted biphenyls of the formula I     or a mixture of IVa and IVb.

Method for producing substituted biphenyls

A process for preparing arylcarboxamides of the formula (I) where with an arylamine (III) in a suitable nonaqueous solvent, wherein, in the absence of an auxiliary base,

Method for manufacturing aryl carboxamides

A process for preparing 1,3-disubstituted pyrazolecarboxylic esters of the formula (I) where where Ris C-C-alkyl at from (&#x2212;41) to (&#x2212;80)&#xb0; C. into an alkyl hydrazine of the formula IIHN&#x2014;NH-lower alkyl &#x2003;&#x2003;(II).

Process for preparing 1,3-disubstituted pyrazolecarboxylic esters

A process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates (VI) where R is methyl or ethyl,from crude reaction mixtures of alkyl 4,4-difluoroacetoacetates (I) by    

Process for preparing alkyl 2-alkoxymethylene-4,4-difluoro-3-oxobutyrates

The present invention relates to a process for preparing 3-difluoromethyl-Substituted pyrazole compounds of the formula (I) in which Ris H, halogen, nitro, C-C-alkyl, C-C-haloalkyl, C-C-cycloalkyl, phenyl, naphthyl, hetaryl, cyano, &#x2014;C(&#x2550;O)&#x2014;OR, &#x2014;C(&#x2550;O)&#x2014;NRR, &#x2014;C(&#x2550;O)&#x2014;SRor &#x2014;C(&#x2550;S)&#x2014;SR; Ris H, C-C-alkyl, benzyl or phenyl; Ris H, halogen, C-C-alkoxy, C-C-haloalkoxy, C-C-cycloalkoxy, C-C-alkenyloxy, C-C-alkylthio, C-C-haloalkylthio, C-C-cyclo-alkylthio or C-C-alkenylthio; compounds of the formula (II.a) or (II.b), in which Rand Reach have one of the definitions given above; Ris halogen, &#x2014;OR, &#x2014;SR, &#x2014;O&#x2014;SO&#x2014;Ror an &#x2014;NRRgroup; Rand Rare each C-C-alkyl, C-C-haloalkyl, C-C-cycloalkyl, benzyl or phenyl, or, together with the nitrogen atom to which they are bonded, are a 3- to 8-membered heterocycle; Lewis acid adducts of compounds of the formula (II.b); the use of compounds of the formula (II.a) or (II.b) and of the Lewis acid adducts for preparing compounds of the formula (I) or (VI);and to a process for converting such compounds to the corresponding 3-difluoro-pyrazol-4-ylcarboxylic acids.

Method for producing difluoromethyl-substituted pyrazole compounds

The present invention relates to a process for preparing N-substituted (3-dihalomethylpyrazol-4-yl)carboxamides of the formula (I) in which Ris optionally substituted phenyl or C-C-cycloalkyl, Ris hydrogen or fluorine, or Rtogether with Ris optionally substituted C-C-alkanediyl or C-C-cycloalkanediyl, Ris C-C-alkyl, C-C-alkenyl, C-C-alkynyl or C-C-alkoxy-C-C-alkyl, X is F or Cl and n is 0, 1, 2 or 3; which comprisesA) providing a compound of the formula (II) in which X is F or Cl, Y is Cl or Br and Rhas one of the meanings given above andB) reacting a compound of the formula (II) with carbon monoxide and a compound of the formula (III) in which R, Rand n have one of the meanings given above; in the presence of a palladium catalyst;to intermediates used for the preparation according to the process according to the invention, and also to processes for their preparation.

Method for the production of N-substituted (3-dihalomethyl-1-methylpyrazol-4-yl) carboxamides

The present invention relates to a process for preparing difluoromethyl-substituted pyrazol-4-ylcarboxylates of the formula I in which in which X is fluorine, chlorine or bromine, Rhas one of the meanings given above and Ris C-C-alkyl, C-C-cycloalkyl, C-C-alkenyl, benzyl or phenyl, is reacted with a silane compound of the general formula RSiClin which n is 1, 2 or 3 and the substituents Rare independently of one another selected from the group consisting of C-C-alkyl and phenyl and with a metal selected from the metals of groups 1, 2, 3, 4 and 12 of the Periodic Table of the Elements having a redox potential of less than &#x2212;0.7 V, based on a normal hydrogen electrode (at 25&#xb0; C. and 101.325 kPa); and

Process for preparing difluoromethylpyrazolyl carboxylates

The present invention relates to a new crystalline form of 3-(Difluormethyl)-1-methyl-N-(3',4&#x2032;,5&#x2032;-trifluor[1,1&#x2032;-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide. The invention also relates to processes for the production of this crystalline form and formulations for plant protection which contain the crystalline form of 3-(Difluormethyl)-1-methyl-N-(3&#x2032;,4&#x2032;,5&#x2032;-trifluor[1,1&#x2032;-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide.

Crystalline form of 3-(difluormethyl)-1-methyl-N-(3',4&#x2032;,5&#x2032;-trifluor[1,1&#x2032;-biphenyl]-2-yl)-1H-pyrazol-4-carboxamide

A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: in which Hal is halogen and X and Rare as defined above, in the presence of a base and of a palladium catalyst selected from the group of:3 in which Rand n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.

Process for preparing substituted biphenyls

A process for preparing substituted biphenyls of the formula I in which the substituents are defined as follows: in which Hal is halogen and X and Rare as defined above, in the presence of a base and of a palladium catalyst selected from the group of: in which Rand n are as defined above, where the triarylphosphines or trialkylphosphines used may be substituted.

Method for the production of 1,3,5-trifluoro-2,4,6-trichlorobenzene from fluorobenzene comprising steps A) and B): A) chlorination of fluorobenzene derivatives of formula (II), in which X=fluorine of H, Z=nitro, bromo or chloro and n=0 or 1-4 and B) fluorination of the distillation residue and separation by distillation of the 1,3,5-trifluoro-2,4,6-trichlorobenzene thus produced. 

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Oftersheim, Germany

Sebastian Peer Smidt