[Cl:1]N1C(=O)CCC1=O.[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20]#[N:21])[CH:14]=[CH:13]2>C(Cl)Cl.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[Cl:1][C:11]1[C:10]([OH:9])=[CH:19][CH:18]=[C:17]2[C:12]=1[CH:13]=[CH:14][C:15]([C:20]#[N:21])=[CH:16]2To 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.
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