Fluorinated Carboxilic Acids and Derivatives

Fluorinated Carboxylic Acid

Fluorinated Acyl Chlorides

Fluorinated Acid Anhydrides

Fluorinated Nitriles

Fluorinated Acrylates and Methacrylates

Introduction

The fluorinated carboxilic acids are strong acids due to the strong electronegativity of the fluorine atom. They have good heat resistance and chemical stability, do not react with general reducing agents and oxidizing agents in aqueous solution. And as important fluorinated building blocks, they are widely used in the synthesis of organic fluorides. For example, fluorinated carboxilic acids can undergo reductive amination reactions to obtain fluorinated amines. They can also synthetize fluorinated aldehydes or fluorinated alcohols through hydrogenation. Fluorinated carboxilic acids can also undergo various conversion reactions to obtain a series of carboxilic acid derivatives. At present, fluorinated carboxilic acids and derivatives have received extensive attention, and their synthesis have become a hot spot in organic chemistry.

Synthesis

There are various methods for the synthesis of fluorinated carboxylic acids and derivatives. The following are some selected methods for the preparation of fluorinated carboxylic acids and derivatives.

• Synthesis of fluorinated carboxylic acids. McNulty et al. described a one-pot method for the synthesis of fluorinated carboxilic acids. They utilized the reaction of a 1,1-bis-dimethylphosphonate derivative with the fluorinated benzaldehyde and controlled acid hydrolysis of the derived a-phosphonoenamine intermediate to obtained fluorinated carboxylic acids through one-pot method^[1]. In 2006, Brigaud et al. developed an efficient straightforward synthetic route for the synthesis of trifluoromethylated carboxylic acids. Using an oxazolidine derived from trifluoroacetaldehyde hemiacetal and (R)-phenylglycinol as starting materials, they obtained fluorinated carboxylic acids in good yields and higher stereoselectivity through Mannich-type reaction^[2].

Fig.1 Synthesis of fluorinated carboxilic acids through one-pot method

Fig.2 Synthesis of fluorinated carboxilic acids through Mannich-type reaction

• Synthesis of fluorinated carboxylic acid derivatives. Fluorinated carboxilic acids can undergo various conversion reactions to obtain a series of fluorinated carboxilic acid derivatives. For example, fluorinated carboxilic acids react with chlorinating agents such as thionyl chloride, phosphorus trichloride and phosphorus pentachloride to generate fluorinated acyl chlorides. In the presence of dehydrating agents, intermolecular dehydration of fluorinated carboxilic acids can generate fluorinated acid anhydrides. Fluorinated carboxilic acids can produce fluorinated nitriles through amidation and dehydration, they can also be dehydrated with alcohols to produce fluorinated esters under acid-catalyzed conditions.

Alfa Chemistry can offer various fluorinated carboxilic acids and derivatives building blocks such as fluorinated acyl chlorides, fluorinated acid anhydrides, fluorinated nitriles and fluorinated acrylates and methacrylates. You can click on our product list for a detailed view. At the same time, we also offer product customization according to customer's detailed requirements. If you are interested in our products, please feel free to contact us. We will be happy to provide you with support and services.

References

1. McNulty, J.; Das, P. Development of a one-pot method for the homologation of aldehydes to carboxylic acids. Tetrahedron. 2009, 65: 7794-7800.
2. Brigaud, T.; Huguenot, F. Convenient asymmetric synthesis of β-trifluoromethyl-β-amino acid, β-amino ketones, and γ-amino alcohols via reformatsky and Mannich-type reactions from 2-trifluoromethyl-1,3-oxazolidines. J. Org. Chem. 2006, 71: 2159-2162.