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

US8586750B2 · kind B2 · utility

Assignee

• BASF SE

Inventors

• Thomas Zierke · Böhl-Iggelheim, DE
• Volker Maywald · Ludwigshafen, DE
• Michael Rack · Eppelheim, DE
• Sebastian Peer Smidt · Mannheim, DE
• Michael Keil · Freinsheim, DE
• Bernd Wolf · Niederkirchen, DE
• Christopher Koradin · Ludwigshafen, DE

Key dates

• Filing date: Apr 30, 2009
• Grant date: Nov 19, 2013
• Expiry date: Feb 12, 2030

Classification

• Technology area (CPC C): Chemistry; Metallurgy
• CPC primary: C07D231/14
• WIPO field: Organic fine chemistry
• WIPO sector: Chemistry

Abstract

The present invention relates to a process for preparing 2-(aminomethylidene)-4,4-dihalo-3-oxobutyric esters of the formula (I),wherein R1, R2, R3 are C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C3-C10-cycloalkyl or benzyl, and/or R2 together with R3 and 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.