1378388-19-2

The general procedure for the synthesis of 7-[(2-bromo-5-chlorophenyl)methoxy]-3,4-dihydro-1(2H)-naphthalenone from 2-bromo-5-chlorobenzyl bromide and 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one was carried out in the following manner: under argon protection, 7-hydroxy-3,4-dihydronaphthalen-1(2H)-one (13.9 g, 85.7 mmol) and 2-bromo-5- chlorobenzyl bromide (25.6 g, 90.0 mmol) were dissolved in dimethylformamide (850 mL) and potassium carbonate (24 g, 172 mmol) was added. The reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (1 L) and washed sequentially with water three times and brine once. The organic layer was dried with magnesium sulfate, filtered and concentrated. Methanol (500 mL) was added to the oil obtained by concentration and stirred for 30 minutes. The solid product was collected by filtration to afford 7-[(2-bromo-5-chlorophenyl)methoxy]-3,4-dihydro-1(2H)-naphthalenone (27.8 g, 89% yield).

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