Chlorosuccinimide → 5-Chloro-6-hydroxynaphthalene-2-carbonitrile

Participants

Reaction Steps

To a cooled (0° C.) solution of N-chlorosuccinimide (1.4 g, 10.4 mmol) in 80 mL of CH2Cl2, ZrCl4 (0.122 g, 5% mol) was added, followed by 6-hydroxynaphthalene-2-carbonitrile (1.76 g, 10.4 mmol). The mixture was stirred for 18 h at room temperature until the complete disappearance of the starting material as judged by GC analysis. The mixture was quenched with saturated NH4Cl aqueous solution (30 mL) and transferred to a separatory funnel. The two phases were separated and the organic one was washed with water (3×10 mL), dried over Na2SO4 and evaporated under vacuum to give a yellow oil. The crude was purified by flash cromatography (petroleum ether/ethyl acetate 75:25) to afford 5-chloro-6-hydroxynaphthalene-2-carbonitrile (1.38 gr, 65% yield), as whitish solid.

Provenance & Evidence