Fluorinated Pyrazolone Synthesis Without O-Substituted By-Products
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Solution Overview
Problem
Existing methods for producing 1,2-disubstituted-3-pyrazolone compounds with a trifluoromethyl group at the 4-position and a specific substituent at the 5-position face challenges in suppressing the formation of O-substituted products as by-products, leading to inefficiencies in production.
Innovation Solution
A method involving the reaction of fluoroisobutanoic acid fluoride or fluoroisobutene derivatives with specific compounds to form fluorine-containing pyrazolone compounds, utilizing fluoride ion scavengers and nucleophilic reagents to achieve high yields of 1,2-disubstituted-3-pyrazolone compounds without O-substituted by-products.
Engineering Contradictions & Design Principles
Engineering Contradiction Analysis
1Manufacturing precision
If a substituent is introduced into the 2-position of the pyrazolone ring using conventional methods, then the desired 1,2-disubstituted-3-pyrazolone compound is produced, but an O-substituted product is formed as a by-product
Solution Approach 1:
The patent changes the reaction parameters by using specific reagents (fluoroisobutanoic acid fluoride or fluoroisobutene derivatives) and controlling reaction conditions (temperature, solvent, catalyst) to suppress the formation of O-substituted by-products while maintaining high yield of the desired 1,2-disubstituted-3-pyrazolone compound
Solution Approach 2:
The patent introduces specific intermediaries such as fluoride ion scavengers and nucleophilic reagents that mediate the substitution reaction at the 2-position of the pyrazolone ring, preventing the oxygen atom from reacting and forming O-substituted by-products
2Ease of manufacture
If conventional substitution methods are used on 3-pyrazolone compounds, then the pyrazolone ring is modified, but the reaction produces harmful by-products that reduce manufacturing efficiency
Solution Approach 1:
The patent converts the potentially harmful reaction pathway that produces O-substituted by-products into a beneficial process by using specific reagents (fluoroisobutanoic acid fluoride or fluoroisobutene derivatives) that selectively react at the 2-position of the pyrazolone ring, eliminating the formation of harmful by-products and improving overall production efficiency
Applied Scientific Principles
This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.
Function Achieved in This Case
The method enables the production of novel fluorine-containing pyrazolone compounds with trifluoromethyl and specific substituents at the 4- and 5-positions, exhibiting excellent biological activities and structural expandability, facilitating fungicidal, insecticidal, and herbicidal effects, and potential use in electronic materials.
Implementation Method 1
reacting a fluoroisobutanoic acid fluoride or a fluoroisobutene derivative with a compound to produce a fluorine-containing pyrazolone compound
Data Source
AI summary
To provide a novel fluorine-containing 1,2-disubstituted-3-pyrazolone compound having a trifluoromethyl group at the 4-position and a specific substituent at the 5-position and a production method capable of simply producing the fluorine-containing pyrazolone compound without the formation of an O-substituted product as a by-product. A fluorine-containing pyrazolone compound represented by the following formula (1): wherein X represents a halogen atom, -OA1, -S(O1)A1, where l is an integer of 0 to 2, -O-NA1A2, -NA1A2, -NA3-NA1A2, or -N=A4; Y and Z each independently represent an aromatic hydrocarbon group having 1 to 12 carbon atoms, an alkyl group, -COA1, -COOA1, a benzyl group, or a carbamoyl group, or Y and Z are bonded to each other to form a ring; and A1, A2, A3, and A4 each independently represent an organic group having 1 to 12 carbon atoms.