The Synthetic Routes of 2-Pyridinecarboxylicacid,5-(trifluoromethyl)-,ethylester

The synthetic routes of 2-pyridinecarboxylicacid,5-(trifluoromethyl)-,ethylester, also known as 5-(trifluoromethyl)-2-pyridylacetate, is a compound used in various chemical reactions and applications.
This compound can be synthesized through multiple methods, each with its own advantages and disadvantages.
This article will discuss two common synthetic routes for this compound.

Route 1: via the reaction of 2-pyridinecarboxylic acid with Trifluoroacetic acid

One common method for synthesizing 5-(trifluoromethyl)-2-pyridylacetate is through the reaction of 2-pyridinecarboxylic acid with trifluoroacetic acid.
This reaction can be carried out using pure reagents in the presence of a solvent such as ether or THF.
The reaction proceeds through the formation of an enolate intermediate, followed by an intramolecular aldol condensation.
The resulting product is then treated with a base, such as sodium hydroxide, to hydrolyze the Trifluoroacetate group and yield the desired ethylester.

Advantages of this route:

• The reaction can be carried out using easily available reagents.
  
• The reaction is relatively simple and can be performed at room temperature, making it economical.
  
• The yield of the product is good.
  

Disadvantages of this route:

• The reaction requires the use of a strong acid, which can be hazardous to handle.
  
• The reaction produces HF, which is a highly toxic and corrosive gas.
  
• The final product needs to be hydrolyzed to remove the trifluoroacetate group, which can be time-consuming and costly.
  

Route 2: via the reaction of 2-Pyridinecarboxylic acid chloride with Trifluoromethyltrimethylsilane

Another method for synthesizing 5-(trifluoromethyl)-2-pyridylacetate is through the reaction of 2-pyridinecarboxylic acid chloride with trifluoromethyltrimethylsilane.
This reaction can be carried out using pure reagents in the presence of a Lewis acid catalyst, such as aluminum chloride.
The reaction proceeds through the formation of a siloxy intermediate, followed by a nucleophilic substitution reaction.
The resulting product is then treated with a base, such as sodium hydroxide, to hydrolyze the trimethylsilyl group and yield the desired ethylester.

Advantages of this route:

• The reaction can be carried out using easily available reagents.
  
• The reaction can be performed at room temperature, making it economical.
  
• The yield of the product is good.
  

Disadvantages of this route:

• The reaction requires the use of a Lewis acid catalyst, which can be expensive and difficult to handle.
  
• The reaction produces a siloxy by-product, which can be difficult to remove.
  
• The final product needs to be hydrolyzed to remove the trimethylsilyl group, which can be time-consuming and costly.
  

In conclusion, the synthetic routes of 2-pyridinecarboxylicacid,5-(trifluoromethyl)-,ethylester are varied and can be chosen based on the specific needs of the application.
Both routes have advantages and disadvantages, and the choice of route will depend on the availability and cost of the reagents, as well as the desired product characteristics.
Regardless of the route chosen, the resulting product can be used in various chemical reactions and applications, such as in the synthesis of pharmaceuticals, agrochemicals, and intermediates for the production of specialty chemicals.