Bromine → 4-Bromo-5-chloro-2-cyanophenol

Participants

Reaction Conditions

Reaction Steps

Methanol (100 ml) was added to sodium acetate (1.97 g) and 5-chloro-2-cyanophenol (1.84 g, mp. 155°-157° C.) which was synthesized according to a known method. The mixture was allowed to cool to -78° C., and to the solution was added dropwise a solution of bromine (1.53 g) in methanol (25 ml). After stirring at -78° C. for 30 minutes, the solvent was distilled off under reduced pressure, and ethyl acetate and aqueous potassium bisulfate solution were added to the residue. The ethyl acetate layer was washed with saturated saline solution, dried over anhydrous magnesium sulfate and the solvent was distilled off. The residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane to obtain 4-bromo-5-chloro-2-cyanophenol (0.53 g, mp. 229°-231° C. (dec.)).

Provenance & Evidence