The Synthetic Routes of B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid

B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid is an important intermediate in the production of various pharmaceuticals and agrochemicals.
This compound is used as a precursor for the synthesis of various derivatives that have potential therapeutic and agronomic applications.
The synthesis of B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid can be accomplished through various synthetic routes, each with its own advantages and disadvantages.
In this article, we will discuss some of the synthetic routes that are commonly used to synthesize this compound in the chemical industry.

1. Hydroboration-oxidation of 2-methylphenyldiethylamine

The first synthetic route that can be used to synthesize B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid is through the hydroboration-oxidation of 2-methylphenyldiethylamine.
This involves the addition of a borane reagent, such as borane-dimethylsulfide or borane-triphenylphosphine, to 2-methylphenyldiethylamine in the presence of a Lewis acid catalyst, such as zinc chloride or aluminum chloride.
The resulting product is then oxidized using hydrogen peroxide or sodium hypochlorite to yield the desired boronic acid.

2. Reduction of 2-[[(2,4-dichlorophenyl)sulfonyl]oxy]-N,N-dimethylethylamine

Another synthetic route that can be used to synthesize B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid is through the reduction of 2-[[(2,4-dichlorophenyl)sulfonyl]oxy]-N,N-dimethylethylamine.
This involves the reduction of the sulfonate ester using a reducing agent such as lithium aluminum hydride or hydrogen in the presence of a catalyst such as palladium on barium oxide or palladium black.

3. Reductive boration of 2-methylphenyldiethylamine

The reductive boration of 2-methylphenyldiethylamine is another synthetic route that can be used to synthesize B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid.
This involves the addition of borane-dimethylsulfide or borane-triphenylphosphine to 2-methylphenyldiethylamine in the presence of a reducing agent such as ascorbic acid or a cyanide source, followed by hydrogenation to yield the desired boronic acid.

4. From 2-methylphenyl-bis-(diethylamino)methane

B-[5-[(Diethylamino)sulfonyl]-2-methylphenyl]boronic acid can also be synthesized from 2-methylphenyl-bis-(diethylamino)methane, which is synthesized by the reaction of 2-methylphenylamine with diethylamine in the presence of a coupling agent such as hydroxyquinoline or dicyclohexylcarbodiimide.
The resulting product is then treated with a borane-containing reagent and hydrogen peroxide to yield the desired boronic acid.

5. From 2-methylphenyl-diethylamine

Another synthetic