695-96-5

White to slightly beige low melting solid

2-Bromo-4-chlorophenol is a reactant in the preparation of 3-(2-(2,4-dichlorophenoxy)ethoxy)-6-methyl-2-nitropyridine selective sphingosine-1-phosphate 4 receptor (S1P4-R) agonist.

The main use of 2-bromo-4-chlorophenol in the pesticide field is as a key intermediate in the synthesis of profenofos. Profenofos is a highly effective broad-spectrum organophosphorus insecticide with contact and stomach poison effects, and also possesses some fumigation activity. It is widely used to control various pests on crops such as cotton and vegetables.

The general procedure for the synthesis of 2-bromo-4-chlorophenol from the compound (CAS:17005-59-3) is as follows: in a 10 mL round-bottomed flask with a magnetic stir bar, phenols or olefins (0.1 mmol), carbon tetrabromide (CBr4, 33 mg, 0.1 mmol), anhydrous acetonitrile (CH3CN, 1 mL), and dichloro tris(2,2'-) bipyridine)ruthenium(II) (Ru(bpy)3Cl2, 3.8 mg, 0.005 mmol). The reaction mixture was irradiated at room temperature using a blue LED lamp (1 W) and air was continuously passed until the complete disappearance of the raw material was shown by thin layer chromatography (TLC). After completion of the reaction, the solvent was removed by distillation under reduced pressure. Finally, the residue was purified by fast column chromatography to obtain the target product 2-bromo-4-chlorophenol.

[1] Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 622 - 627