The Production Process of 9,9'-Spirobi[9H-fluorene]-4-ylboronicacid

The production process of 9,9'-spirobi[9H-fluorene]-4-ylboronic acid is a complex and multi-step process that involves several chemical reactions and purification steps.
In this article, we will discuss the production process of 9,9'-spirobi[9H-fluorene]-4-ylboronic acid in detail.

Step 1: Synthesis of 4-chloromethylbiphenyl-3-ylboronic acid
The first step in the production process of 9,9'-spirobi[9H-fluorene]-4-ylboronic acid is the synthesis of 4-chloromethylbiphenyl-3-ylboronic acid.
This compound is synthesized by the reaction of 4-chloromethylbiphenyl-3-one with boron tribromide in the presence of a solvent such as toluene.
The reaction is exothermic and requires careful temperature control to avoid unwanted side reactions.

Step 2: Reduction of 4-chloromethylbiphenyl-3-ylboronic acid to 4-chloromethylbiphenyl-3-ol
The next step in the production process is the reduction of 4-chloromethylbiphenyl-3-ylboronic acid to 4-chloromethylbiphenyl-3-ol.
This reduction is carried out using a reducing agent such as lithium aluminum hydride (LiAlH4) in the presence of a solvent such as 1,4-dioxane.
The reaction is exothermic and requires careful temperature control to avoid unwanted side reactions.

Step 3: Reductive couple of 4-chloromethylbiphenyl-3-ol with 9-(2,3-dihydrobenzo[l,2,3]dioxol-5-yl)-9H-fluorene-2-boronic acid
In this step, 9-(2,3-dihydrobenzo[l,2,3]dioxol-5-yl)-9H-fluorene-2-boronic acid is coupled with 4-chloromethylbiphenyl-3-ol in the presence of a palladium catalyst and a solvent such as dichloromethane.
The reaction is carried out at a low temperature to avoid unwanted side reactions.

Step 4: Purification of the resulting product
The resulting product from the previous step is a mixture of different isomers, which need to be purified before further processing.
This purification is typically done using chromatography techniques such as high-performance liquid chromatography (HPLC) or flash chromatography.

Step 5: Nucleophilic substitution of 4-chloromethylbiphenyl-3-ol with 9,9'-spirobi[9H-fluorene]-4-ol
In this step, 9,9'-spirobi[9H-fluorene]-4-ol is reacted with 4-chloromethylbiphenyl-3-ol in the presence of a strong base such as sodium hydroxide and a solvent such as DMF.
The reaction is carried out at a high temperature to accelerate the reaction.

Step 6: Purification of the resulting product
The resulting product from the previous step is a mixture of different isomers, which need to be purified before further processing.
This purification is typically done using chromatography techniques such as HPLC or flash chromatography.

Step 7: Reduction of 9,9'-spirobi[9H-fluorene]-4-ylboronic acid to 9,9'-spirobi[9H-fluorene]-4-ol
The final step in the production process of 9,9'-spirobi[9H-flu