The Production Process of 2-Bromo-9,9′-spirobi[9H-fluorene]

The 2-Bromo-9,9′-spirobi[9H-fluorene] is an important intermediate in the production of a wide range of fluorene-based chemicals, which are used in various applications such as in the manufacture of pharmaceuticals, agrochemicals, and electronic materials.
The production process of 2-Bromo-9,9′-spirobi[9H-fluorene] involves several steps, including the preparation of the starting materials, the reaction, and the purification of the product.

1. Preparation of the starting materials:

The preparation of the starting materials is the first step in the production of 2-Bromo-9,9′-spirobi[9H-fluorene].
The starting material for the production of 2-Bromo-9,9′-spirobi[9H-fluorene] is 9,9′-spirobi[9H-fluorene], which is a white crystalline solid with a molecular formula C12H8Cl2F2.
9,9′-spirobi[9H-fluorene] is synthesized by azo coupling reaction between o-phenylenediamine and β-chloroethyldichloride in the presence of sodium hydroxide.

2. Reaction:

The next step in the production of 2-Bromo-9,9′-spirobi[9H-fluorene] involves the reaction of 9,9′-spirobi[9H-fluorene] with N-bromosuccinimide (NBS) in the presence of a solvent such as acetonitrile or benzene.
The reaction is exothermic and generates a significant amount of heat, which must be removed to avoid any unwanted decomposition of the reaction mixture.
The reaction is typically carried out at a temperature range of 50-60°C, and the reaction time is usually between 2-4 hours.
The molar ratio of 9,9′-spirobi[9H-fluorene] to NBS is typically 1:3.

3. Purification:

After the reaction, the product is purified to remove any impurities that may have been introduced during the reaction.
The purification is typically carried out by precipitation with a hydrophilic solvent such as ether or methanol.
The precipitated product is then filtered and dried to remove any remaining impurities.
The purified 2-Bromo-9,9′-spirobi[9H-fluorene] is then further characterized by techniques such as spectroscopy and chromatography to ensure its purity and identity.

4. Characterization:

The final step in the production of 2-Bromo-9,9′-spirobi[9H-fluorene] involves its characterization.
This involves various techniques such as spectroscopy (FTIR, NMR) and chromatography (TLC, HPLC) to determine the purity, identity, and molecular structure of the product.

In conclusion, the production of 2-Bromo-9,9′-spirobi[9H-fluorene] is a multi-step process that requires careful monitoring and control of reaction conditions to ensure the desired product is obtained.
The resulting product is then further characterized to ensure its purity and identity.
The product can be used as an intermediate in the production of various chemicals, such as pharmaceuticals, agrochemicals, and electronic materials.