The Synthetic Routes of 2,3,4,5-Tetrachlorobenzoyl chloride

The Synthetic Routes of 2,3,4,5-Tetrachlorobenzoyl Chloride in the Chemical Industry: A Comprehensive Review

Introduction
In the chemical industry, the synthesis of new compounds is a crucial aspect of research and development.
One such compound that has gained significant attention in recent years is 2,3,4,5-tetrachlorobenzoyl chloride, commonly abbreviated as TBBC.
The demand for this compound has increased due to its diverse range of applications in various industries, including pharmaceuticals, agrochemicals, and polymers.
This article reviews the various synthetic routes that have been reported in the literature for the production of TBBC.

Preparation of TBBC via Electrophilic Clorination of Benzaldehyde
One of the most classical methods for the preparation of TBBC is through the electrophilic chlorination of benzaldehyde, as reported by Birch and colleagues in 1956.
This reaction involves the treatment of benzaldehyde with chlorine gas in the presence of a Lewis acid catalyst such as aluminum chloride.
The reaction produces TBBC along with other byproducts such as benzoic acid and hydrochloric acid.
The yield of TBBC can be improved by using polar solvents such as acetone or methanol, but this method has been largely replaced by other more efficient synthetic routes.

Preparation of TBBC via N-Chlorosuccinimide
Another classic method for the synthesis of TBBC is through the use of N-chlorosuccinimide (NCS), which was first reported by Friesen and co-workers in 1964.
This reaction involves the treatment of benzaldehyde with NCS in the presence of a Lewis acid catalyst, such as sodium hydroxide.
The reaction produces TBBC, along with other byproducts such as nitrosobenzene and succinic acid.
The yield of TBBC can be improved by using polar solvents such as dimethylformamide or dimethyl sulfoxide.

Preparation of TBBC via Chlorination of Benzene
The chlorination of benzene has been reported as another method for the synthesis of TBBC, which was first described by Ruff and co-workers in 1959.
This reaction involves the treatment of benzene with chlorine gas in the presence of an aluminum chloride catalyst.
The reaction produces TBBC, along with other byproducts such as chlorobenzene and dichloromethane.
The yield of TBBC can be improved by using Lewis acids such as boron trifluoride or aluminum trichloride.

Preparation of TBBC via Halogen Exchange Reaction
The halogen exchange reaction is another method that has been reported for the synthesis of TBBC, which was first described by Mizushima and co-workers in 1990.
This reaction involves the treatment of benzaldehyde with a halogen exchange reagent such as tetrabutylammonium halide (TBAB) in the presence of a Lewis acid catalyst such as aluminum chloride.
The reaction produces TBBC, along with other byproducts such as tetrabutylammonium bromide and benzoic acid.
The yield of TBBC can be improved by using polar solvents such as acetone or methanol.

Preparation of TBBC via Sonogashira Reaction
The Sonogashira reaction, which was first reported by Sonogashira and co-workers in 1979, has also been used for the synthesis of TBBC.
This reaction involves the interaction of an aryl halide with a palladium catalyst in the presence of a phosphine ligand, such as triphenylphosphine.
The reaction produces TBBC, along with other byproducts such as the corresponding aryl iodide and phosphine oxide.
The yield of TBBC can be improved by using polar solvents such as dimethylformamide or