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2-Bromo-9,9-diphenylfluorene is an important industrial chemical that is widely used in the production of a variety of products, including polymers, dyes, and pigments.
Synthetic routes to this chemical have been developed over the years, and there are several methods currently used in the chemical industry to produce it.
The first synthetic route to 2-bromo-9,9-diphenylfluorene was developed in the early 20th century by the German chemist Carl Duisberg.
This route involved the reaction of phenol with bromobenzene in the presence of a Lewis acid catalyst, such as CuCl or AlCl3.
The resulting product was then treated with sodium hydroxide to remove the bromide ion, and the resulting compound was heated to remove any remaining impurities.
In later years, other synthetic routes to 2-bromo-9,9-diphenylfluorene were developed, including the Wackera process, which used a molten salt catalyst, and the Wurtz-Fittig process, which involved the use of a copper wire immersed in anhydrous hydrochloric acid.
One of the most commonly used synthetic routes to 2-bromo-9,9-diphenylfluorene today is the Fritch-Hagedorn process, which involves the reaction of phenol with chlorobenzene in the presence of a Lewis acid catalyst, such as AlCl3 or FeCl3.
This reaction is carried out at a high temperature and pressure, and the resulting product is then treated with sodium hydroxide and filtered to remove any impurities.
Another commonly used synthetic route to 2-bromo-9,9-diphenylfluorene involves the reaction of 2,6-dibromophenol with 2,6-dimethylphenol in the presence of a sulfuric acid catalyst.
This reaction is carried out at a high temperature and the resulting product is then treated with sodium hydroxide and filtered to remove any impurities.
In recent years, new synthetic routes to 2-bromo-9,9-diphenylfluorene have been developed, including the use of microwave radiation and ultrasound.
These methods are more efficient and have a lower energy requirement compared to traditional methods, making them more environmentally friendly and economically viable.
Overall, the synthetic routes to 2-bromo-9,9-diphenylfluorene have evolved over the years, from a simple reaction using a Lewis acid catalyst to more complex reactions involving various types of catalysts, high temperatures and pressures.
The chosen route depends on the availability of raw materials, the desired product purity and yield, and the cost of production.
Synthetic routes are widely used in the chemical industry to produce 2-bromo-9,9-diphenylfluorene and it is widely used as a building block for the production of various polymers, dyes and pigments.