The Production Process of TERT-BUTYL 7-BROMO-3,4-DIHYDROISOQUINOLINE-2(1H)-CARBOXYLATE

The production process of tert-butyl 7-bromo-3,4-dihydroisoquinolette-2(1H)-carboxylate, also known as TBDIC, involves a series of chemical reactions that convert starting materials into the desired product.
TBDIC is a versatile intermediate that is commonly used in the synthesis of various pharmaceuticals, agrochemicals, and other chemical products.

The production process of TBDIC can be divided into several steps, including the preparation of starting materials, the reaction steps, and the purification and isolation of the final product.
The specific steps involved in the production process may vary depending on the scale of production, the purity of the starting materials, and the specific requirements of the final product.

Preparation of Starting Materials

The production of TBDIC typically starts with the preparation of starting materials, which are typically derived from petrochemical sources.
One of the key starting materials is 2,3-dimethyl-2,3-dihydro-1H-isoindole-1,2-dione, also known as DDDI.
This compound is typically obtained by hydrolyzing the condensation product of formaldehyde and phenol, followed by a sequence of chemical reactions to remove impurities and residual reagents.

Another key starting material is 2-bromo-3-tert-butyl-5-hydroxy-benzaldehyde, also known as BTBAL.
This compound is typically prepared by a multi-step reaction sequence that involves the condensation of salicylaldehyde with acetaldehyde, followed by nitration, sulfonation, and bromination reactions.

Reaction Steps

Once the starting materials are prepared, the next step in the production of TBDIC is the reaction steps that convert the starting materials into the desired product.
The specific reaction steps involved in the synthesis of TBDIC can vary depending on the manufacturing process, but typically involve a series of chemical reactions such as condensation, nitration, sulfonation, bromination, and reduction.

The condensation reaction involves the reaction of 2,3-dimethyl-2,3-dihydro-1H-isoindole-1,2-dione with 2-bromo-3-tert-butyl-5-hydroxy-benzaldehyde in the presence of a condensation agent such as pyridine, followed by gentle heating to drive off any remaining pyridine.

The nitration reaction involves the addition of nitrating agent such as nitric acid to the condensation product, followed by heating to remove water and complete the nitration reaction.

The sulfonation reaction involves the addition of a sulfonating agent such as sulfuric acid to the nitrated product, followed by gentle heating to drive off any remaining sulfuric acid.

The bromination reaction involves the addition of a brominating agent such as N-bromosuccinimide to the sulfonated product, followed by gentle heating to drive off any remaining brominating agent.

The reduction reaction involves the addition of a reducing agent such as lithium aluminum hydride to the brominated product, followed by gentle heating to reduce the bromine atom to a hydrogen atom.

The final step in the production of TBDIC is the purification and isolation of the final product.
This typically involves a series of steps such as filtration, washing, and crystallization to remove any impurities and isolate the pure product.

Purification and Isolation of the Final Product

The purification and isolation of the final product is a critical step in the production process of TBDIC.
This step typically involves a series of