Title:
NEW PROCESS FOR THE SYNTHESIS OF 5-FLUORO-3- (DIFUOROMETHYL) -5-FLUORO-1-METHYL-1H-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES AND THE FREE ACID THEREOF
Document Type and Number:
WIPO Patent Application WO/2022/233129
Kind Code:
A1
Abstract:
Provided is a new process for the synthesis of 5-fluoro-3- (difluoromethyl) -5-fluoro-1-methyl-1Hpyrazole-4-carboxylic acid derivatives and the free acid thereof, involving a direct fluorination reaction with a fluorination gas comprising or consisting of elemental fluorine (F2), in a reactor which is resistant to elemental fluorine (F2) and hydrogen fluoride (HF), and wherein in the process as a starting material a difluoromethylpyrazole compound dissolved in an inert solvent is subjected to the direct fluorination reaction. Some particular examples of 5-fluoro-3- (difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid derivatives which can be prepared according to the process of the invention are 3-(difluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid fluoride (5FDFMPAF), also known under the alternative name 3- (difluoromethyl) -5-fluoro -1-methyl-1H-pyrazole-4-carbonyl fluoride; 3- (difluoromethyl)-5-fluoro-1-methyl- 1H-pyrazole-4-carboxylic acid ethylester (5FDFMP); and 3- (chlorodifluoromethyl) -5-fluoro-1-methyl-1H-pyrazole-4-carboxylic acid ethylester (5FCDFMP), or the corresponding methyl esters. The 5-fluoro-3- (difluoromethyl) -5-fluoro-1-methyl -1H-pyrazole-4-carboxylic acid can be obtained from its carboxylic acid derivatives such as, e.g., mentioned before in that the acid derivative is converted to the corresponding carboxylic acid.
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Inventors:
CUI WEILONG (CN)
LUO WEIFEN (CN)
WU WENTING (CN)
LUO WEIFEN (CN)
WU WENTING (CN)
Application Number:
PCT/CN2021/134408
Publication Date:
November 10, 2022
Filing Date:
November 30, 2021
Export Citation:
Assignee:
FUJIAN YONGJING TECH CO LTD (CN)
International Classes:
C07D231/16; C07B39/00
Domestic Patent References:
WO2020093715A1 | 2020-05-14 | |||
WO2011061205A1 | 2011-05-26 | |||
WO2003000686A1 | 2003-01-03 | |||
WO2004014138A1 | 2004-02-19 | |||
WO2015110493A1 | 2015-07-30 | |||
WO2011131615A1 | 2011-10-27 | |||
WO2016016298A1 | 2016-02-04 | |||
WO2012010692A1 | 2012-01-26 | |||
WO2008053043A1 | 2008-05-08 |
Foreign References:
CN103140477A | 2013-06-05 | |||
JP2009126828A | 2009-06-11 | |||
CN111349018A | 2020-06-30 | |||
EP2920151A1 | 2015-09-23 | |||
EP1637271B1 | 2011-05-18 | |||
EP2008996A1 | 2008-12-31 | |||
EP0623575A1 | 1994-11-09 | |||
CN103214355A | 2013-07-24 | |||
CN111349018A | 2020-06-30 |
Other References:
MAKINO, K. ; YOSHIOKA, H.: "Selective fluorination of ethyl 1-methylpyrazole-4-carboxylates with poly(hydrogen fluoride)-amine complex under electrolytic anodic oxidation", JOURNAL OF FLUORINE CHEMISTRY, ELSEVIER, NL, vol. 39, no. 3, 1 June 1988 (1988-06-01), NL , pages 435 - 440, XP028086748, ISSN: 0022-1139, DOI: 10.1016/S0022-1139(00)81615-2
JOURNALPEST MANAGSCI, vol. 76, 2020, pages 3340 - 3347
ORGANIC PROCESS RESEARCH & DEVELOPMENT (OPRD, vol. 18, 2014, pages 1055 - 1059
JOURNALPEST MANAGSCI, vol. 76, 2020, pages 3340 - 3347
ORGANIC PROCESS RESEARCH & DEVELOPMENT (OPRD, vol. 18, 2014, pages 1055 - 1059
Attorney, Agent or Firm:
FUZHOU GEMHOPE PATENT AGENCY (CN)
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