[Cl:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:11]([OH:20])=[CH:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2>ClCCl.[Cl-].[Zr+4].[Cl-].[Cl-].[Cl-]>[Cl:1][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:19]=[C:10]([CH3:9])[C:11]=1[OH:20]To a solution of N-chlorosuccinimide (8.02 g, 60.05 mmol) in dichloromethane (475 mL) at −78° C. was added zirconium(IV) chloride (2.80 g, 12.01 mmol), followed by 3-methyl-naphthalen-2-ol (CombiBlocks, 9.5 g, 60.05 mmol) under argon. The reaction mixture was stirred at −78° C. for 5 minutes, the cooling bath was removed and the reaction was stirred at room temperature for 5 h. The reaction was quenched with saturated sodium bicarbonate solution and stirred for 5 minutes. The mixture was diluted with H2O, extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 10% ethyl acetate/hexanes) to give 1-chloro-3-methyl-naphthalen-2-ol.
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