Patent ID: 8288582

Claim:
A process for preparing a 2-fluoroacyl-3-aminoacrylic acid derivative of formula (I) in which R 1 and R 2 are each independently 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, each of which may be substituted by one or more groups selected from the group consisting of â€”Râ€², â€”X, â€”ORâ€², â€”SRâ€², â€”NRâ€² 2 , â€”SiRâ€² 3 , â€”COORâ€², â€”(Câ•O)Râ€², â€”CN and â€”CONR 2 â€², where Râ€² is hydrogen or a C 1-12 -alkyl group; or R 1 and R 2 , together with the nitrogen atom to which they are bonded, may form a 5- to 6-membered ring which may optionally contain one or two further heteroatoms selected from the group consisting of O, S and SO 2 , and which may be substituted by one or more groups selected from the group consisting of â€”Râ€², â€”X, â€”ORâ€², â€”SRâ€², â€”NRâ€² 2 , â€”SiRâ€² 3 , â€”COORâ€², â€”(Câ•O)Râ€², â€”CN and â€”CONR 2 â€², where Râ€² is hydrogen or a C 1-12 -alkyl group; Y is selected from the group consisting of (Câ•O)OR 3 , CN and (Câ•O)NR 4 R 5 , where R 3 , R 4 and R 5 are each independently 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 â€”Râ€², â€”X, â€”ORâ€², â€”SRâ€², â€”NRâ€² 2 , â€”SiRâ€² 3 , â€”COORâ€², â€”(Câ•O)Râ€², â€”CN and â€”CONR 2 â€², where Râ€² is hydrogen or a C 1-12 -alkyl group; and X 1 and X 2 are each independently fluorine, chlorine, bromine, 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 or C 7-19 -alkylaryl groups, where the aforementioned alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl and alkylaryl groups may each be substituted by one or more groups selected from the group consisting of â€”Râ€², â€”X, â€”ORâ€², â€”SRâ€², â€”NRâ€² 2 , â€”SiRâ€² 3 , â€”COORâ€², â€”(Câ•O)Râ€², â€”CN and â€”CONR 2 â€², where Râ€² is hydrogen or a C 1-12 -alkyl group; comprising reacting a fluorinated carboxylic acid of formula (II) in which X 1 and X 2 are each as defined above, with a 3-aminoacrylic acid derivative of the formula (III) in which R 1 , R 2 and Y are each as defined above, and, in the presence of a base, with an acid halide of the formula (IV) in which R 9 is selected from the group consisting of C 1-12 -alkyl, C 3-8 -cycloalkyl, C 2-12 -alkynyl, C 2-12 -alkynyl, C 6-8 -aryl, C 7-19 -arylalkyl- and C 7-19 -alkylaryl, each of which may be substituted by one or more groups selected from the group consisting of â€”Râ€², â€”X, â€”ORâ€², â€”SRâ€², â€”NRâ€² 2 , â€”SiRâ€² 3 , â€”COORâ€², â€”(Câ•O)Râ€², â€”CN and â€”CONR 2 â€², where Râ€² is hydrogen or a C 1-12 -alkyl group; and Hal is halogen.