What are the Chemical Properties of 3-Bromo-6-Chloro-2-Fluoro Iodobenzene?

3-Bromo-6-Chloro-2-Fluoro Iodobenzene is a polyhalogenated benzene compound with excellent chemical reactivity. It has poor solubility in water but good solubility in common organic solvents. The chemical structure of 3-Bromo-6-Chloro-2-Fluoro Iodobenzene contains multiple halogen atoms, allowing it to participate in various chemical transformation reactions. It is mainly used as an intermediate in organic synthesis and pharmaceutical chemical raw materials, with applications in the synthesis of highly functionalized benzene ring functional organic molecules.

Chemical Properties

The chemical reactivity of 3-Bromo-6-Chloro-2-Fluoro Iodobenzene is mainly focused on the halogen atoms in its structure. The fluorine atom on the benzene ring can undergo aromatic nucleophilic substitution reactions with strong nucleophilic reagents to obtain corresponding deiodinated functionalized derivatives. The iodine and bromine atoms in the structure of 3-Bromo-6-Chloro-2-Fluoro Iodobenzene can undergo cross-coupling reactions catalyzed by transition metals, and the differential reactivity of bromine and iodine atoms allows for stepwise and selective cross-coupling reactions.

Aromatic Nucleophilic Substitution Reaction

Figure 1: Aromatic Nucleophilic Substitution Reaction of 3-Bromo-6-Chloro-2-Fluoro Iodobenzene

In a dry reaction flask, dissolve imidazole in dry N,N-dimethylformamide solution, then add strong base potassium tert-butoxide to the solution. The resulting reaction mixture is stirred at room temperature for an hour. Then add 3-Bromo-6-Chloro-2-Fluoro Iodobenzene to the reaction mixture, heat the resulting mixture to 100 degrees and stir at this temperature for several hours. Monitor the reaction progress by TLC plate, cool the reaction mixture to room temperature after the reaction is complete, dilute with water (50ml), and extract the reaction mixture with CH2Cl2 (40 mL). Dry the combined organic layer on Na2SO4, filter off the drying agent, and concentrate the filtrate under reduced pressure. The residue obtained is purified by silica gel column chromatography to obtain the target product molecule.

Chemical Applications

The chemical structure of 3-Bromo-6-Chloro-2-Fluoro Iodobenzene contains multiple halogen atoms, mainly used as an organic synthesis intermediate. Research reports suggest that this substance can be used for structural modification and synthesis of organic optoelectronic materials, with wide applications in basic chemical research.

References

[1] LG Chem Ltd. Korea Patent, Patent number: KR2017108894 A.