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3-Fluoro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinonitrile is an organic compound that is widely used in various industrial applications.
In the following article, we will discuss the synthetic routes of this compound, which is also known by its chemical name 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)picolinonitrile.
Synthetic routes refer to the methods used in the laboratory to prepare a specific compound.
These routes can vary depending on the starting materials, reaction conditions, and the desired product.
In the case of 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)picolinonitrile, there are several synthetic routes that have been reported in the scientific literature.
In this article, we will discuss three of the most commonly used synthetic routes for this compound.
Route 1: Via Boronic Acid-Based Condensation
The first synthetic route for 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)picolinonitrile involves a boronic acid-based condensation reaction.
In this route, 2-bromo-5-methylthiophene is treated with sodium boronate in the presence of a base such as potassium hydroxide.
The reaction produces a boronic ester intermediate, which is then treated with a nitrile source, such as aqua ammonia, to form the desired product.
This synthetic route has been reported in the scientific literature and is a commonly used method for preparing boronic acid derivatives.
Route 2: Via Palladium-Catalyzed Cross-Coupling
The second synthetic route for 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)picolinonitrile involves a palladium-catalyzed cross-coupling reaction.
In this route, a boronic acid derivative is treated with a titanium halide and a phosphine ligand in the presence of a palladium catalyst.
The reaction produces the desired product, which can be further converted to the target compound via boronic acid-based condensation or other chemical reactions.
This synthetic route is known for its high efficiency and selectivity, and it has been widely used in the synthesis of organic compounds.
Route 3: Via Boronic Ester Hydrolysis
The third synthetic route for 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)picolinonitrile involves boronic ester hydrolysis.
In this route, a boronic ester intermediate is treated with water in the presence of a base such as sodium hydroxide.
The reaction produces the desired product, which can be further converted to the target compound via boronic acid-based condensation or other chemical reactions.
This synthetic route is a simple and efficient method for preparing boronic acid derivatives and has been reported in the scientific literature.
Conclusion
In conclusion, there are several synthetic routes for preparing 2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)picolinonitrile, and each route has its own advantages and disadvantages.
The