Title:
METHOD OF PREPARING 3-FLUOROALKYL-1-METHYLPYRAZOLE-4-CARBOXYLIC ACID
Document Type and Number:
WIPO Patent Application WO/2017/054112
Kind Code:
A1
Abstract:
The present invention relates to a method of preparing a 3-fluoroalkyl-1-methylpyrazole-4-carboxylic acid comprising the following steps: Step 1, performing a condensation reaction on the fluoroacetyl halide derivative shown in formula I and dimethylamino vinyl methyl ketone to produce a 3-dimethylaminomethylene-1,1-difluoro-2,4-pentanedione derivative as shown in formula II; Step 2, performing a ring-closing reaction on the 3-dimethylaminomethylene-1,1-difluoro-2,4-pentanedione derivative shown in formula II and methyl hydrazine to produce a 3-fluoroalkyl-1-methyl-4-acetylpyrazole derivative shown in formula III; Step 3, oxidizing in alkaline conditions the 3-fluoroalkyl-1-methyl-4-acetylpyrazole derivative shown in formula III, and performing reacidification to produce the 3-fluoroalkyl-1-methylpyrazole-4-carboxylic acid shown in formula IV. The reaction path of the preparation method of the present invention is short, has low raw material costs, each step thereof has a high reaction rate, and the method is suitable for industrialized production.
Inventors:
WANG MINGCHUN (CN)
LI QINGYI (CN)
LI QINGYI (CN)
Application Number:
PCT/CN2015/090970
Publication Date:
April 06, 2017
Filing Date:
September 28, 2015
Export Citation:
Assignee:
CHANGZHOU KEYLAB BIOCHEMICAL CO LTD (CN)
SOLVAY FLUOR GMBH (DE)
SOLVAY FLUOR GMBH (DE)
International Classes:
C07D231/14; C07C221/00; C07C225/14; C07C251/30; C07D231/12
Domestic Patent References:
| WO2009010871A2 | 2009-01-22 |
Foreign References:
| CN105541716A | 2016-05-04 | |||
| CN101796021A | 2010-08-04 | |||
| CN101687806A | 2010-03-31 | |||
| CN101115723A | 2008-01-30 | |||
| CN101874029A | 2010-10-27 |
Other References:
CHEN, QIAN ET AL.: "Synthesis of 1-Methyl-3-(trifluoromethyl)-1H-pyrazole-4-carbonyl Chloride", PESTICIDES, vol. 51, no. 8, 31 August 2012 (2012-08-31), pages 569 - 572
LI, LIFENG ET AL.: "Synthesis of 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid", FINE CHEMICAL INTERMEDIATES, vol. 43, no. 6, 31 December 2013 (2013-12-31), pages 17 - 19 and 47
SINGH, S.P. ET AL.: "A Facile Synthesis of 5-Methyl-1-(phenyl/heterocyctr-4-trifluoroacetylpyrazoles", J. CHEM. RESEARCH (S, 1 January 1997 (1997-01-01), pages 142 and 143
LI, LIFENG ET AL.: "Synthesis of 3-difluoromethyl-1-methyl-1H-pyrazol-4-carboxylic acid", FINE CHEMICAL INTERMEDIATES, vol. 43, no. 6, 31 December 2013 (2013-12-31), pages 17 - 19 and 47
SINGH, S.P. ET AL.: "A Facile Synthesis of 5-Methyl-1-(phenyl/heterocyctr-4-trifluoroacetylpyrazoles", J. CHEM. RESEARCH (S, 1 January 1997 (1997-01-01), pages 142 and 143
Attorney, Agent or Firm:
NANJING TONGZE PATENT AGENCY FIRM (LIMITED LIABILITY PARTNERSHIP) (CN)
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