1590-25-6

861880-64-0

75-16-1

1590-25-6

Under nitrogen protection, 6-bromo-N-methoxy-N-methyl-2-naphthalenecarboxamide (82.9 g, 282 mmol, 1.0 eq.) was dissolved in tetrahydrofuran (600 mL) in a four-necked flask. The reaction mixture was cooled in an ice bath at a controlled temperature in the range of 10-15 °C. Methylmagnesium bromide (3.2 M in methyltetrahydrofuran, 197 mL, 2.2 eq.) was added slowly dropwise over a period of 1 hour. After the dropwise addition was completed, the reaction mixture continued to be stirred in an ice bath for 30 minutes. Subsequently, aqueous 2M hydrochloric acid (100 mL) was carefully added dropwise to quench the reaction under cooling in the ice bath. After the organic solvent was removed by evaporation, the precipitated product was extracted with dichloromethane (500 mL). The organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting solid residue was dried under vacuum at 40 °C to give 1-(6-bromonaphthalen-2-yl)ethanone (70.6 g, 99% yield).