FIELD: chemistry.
SUBSTANCE: invention relates to an improved method of producing a fluorine-containing acylacetic acid derivative of formula (3) involving preparation of a mixture containing a base, a compound of formula (1) and a compound of formula (2) and adding a halogenating agent to the mixture, where Rf is an alkyl group having 1-6 carbon atoms which is substituted by at least one fluorine atom; where R1 and R2 each independently represents an alkyl group having 1-6 carbon atoms; R3 is a hydrogen atom; and R4 is an alkyl group having 1-6 carbon atoms; where Rf, R1, R2, R3 and R4 represent the same as given above. The invention also relates to a method of producing a fluorine-containing pyrazolecarboxylic acid ester derivative of formula (5), involving the following steps: - obtaining a mixture containing a base, a compound of formula (1) and a compound of formula (2), and adding a halogenating agent to the mixture, where Rf is an alkyl group having 1-6 carbon atoms which is substituted by at least one fluorine atom; where R1 and R2 each independently represents an alkyl group having 1-6 carbon atoms; R3 is a hydrogen atom; and R4 is an alkyl group having 1-6 carbon atoms; to obtain a fluorine-containing acylacetic acid derivative of formula (3), where Rf, R1, R2, R3 and R4 represent the same as given above; - reaction of the obtained compound of formula (3) with a compound of formula (4) where R5 is an alkyl group having 1-6 carbon atoms, to obtain a compound of formula (5) where Rf, R3, R4 and R5 represent the same as given above; and a method of producing a fluorine-containing pyrazolecarboxylic acid derivative of formula (6) involving the following steps: - obtaining a mixture containing a base, a compound of formula (1) and a compound of formula (2), and adding a halogenating agent to the mixture, where Rf is an alkyl group having 1-6 carbon atoms which is substituted by at least one fluorine atom; where R1 and R2 each independently represents an alkyl group having 1-6 carbon atoms; R3 is a hydrogen atom; and R4 is an alkyl group having 1-6 carbon atoms; to obtain a fluorine-containing acylacetic acid derivative of formula (3), where Rf, R1, R2, R3 and R4 represent the same as given above; - reaction of the obtained compound of formula (3) with a compound of formula (4), where R5 is an alkyl group having 1-6 carbon atoms, to obtain a compound of formula (5), where Rf, R3, R4 and R5 represent the same as given above; -hydrolysis of the compound of formula (5) to obtain a compound of formula (6), where Rf, R3 and R5 represent the same as given above. Addition of a halogenating agent at the last step facilitates the desired reaction with good output.
EFFECT: improved method of producing a fluorine-containing acylacetic acid derivative.
6 cl, 7 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD FOR PREPARING PYRAZOLE-CARBOXYLIC ACID DERIVATIVES | 2013 |
|
RU2638112C2 |
METHOD FOR PRODUCING FLUORINE-CONTAINING ORGANIC COMPOUND | 2021 |
|
RU2807182C1 |
PRODUCTION OF THE FLUORINE-CONTAINING COMPOUNDS | 2002 |
|
RU2285686C2 |
METHOD FOR PREPARING SULFUR-CONTAINING IMIDAZOLE DERIVATIVES AND INTERMEDIATE PRODUCTS | 1993 |
|
RU2135475C1 |
DERIVATIVES OF 5-AMINO-4-HYDROXYHEXANOIC ACID AND A METHOD OF THEIR SYNTHESIS | 1992 |
|
RU2067585C1 |
METHOD OF PRODUCING 3-DIHALOMETHYL-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES | 2007 |
|
RU2470015C2 |
DERIVATIVES OF BUTADIENE AND METHOD OF THEIR SYNTHESIS, DERIVATIVES OF AMIDOBUTADIENE AND METHOD OF THEIR SYNTHESIS, DERIVATIVES OF PYRROLIDINE AND METHOD OF THEIR SYNTHESIS | 1997 |
|
RU2167863C2 |
PYRIDAZINONE DERIVATIVES AND METHODS OR PREPARING THEREOF | 1996 |
|
RU2131419C1 |
METHOD OF PRODUCING ISOTHIAZOLE DERIVATIVES | 2005 |
|
RU2349588C2 |
PYRAZINE DERIVATIVES AND THEIR ACID-ADDITIVE SALTS | 1992 |
|
RU2124008C1 |
Authors
Dates
2012-07-20—Published
2009-03-11—Filed