1. To a solution of 2-chloro-6-hydroxybenzonitrile (614 mg, 4 mmol) in tetrahydrofuran (THF, 10 mL) under argon protection is slowly added a solution of methylmagnesium bromide in toluene/THF (3:1, 1.4 M, 6.4 mL, 9 mmol). Note: Gas escapes during the reaction.
2. Stir the reaction mixture at room temperature until the escape of gas ceases.
3. Transfer the reaction mixture to a sealed tube and stir overnight at 65°C. 4.
4. upon completion of the reaction, the reaction is quenched with water and acidified with aqueous hydrochloric acid.
5. The organic layer containing 1-(2-chloro-6-hydroxyphenyl)ethanone was extracted with dichloromethane (DCM).
6. The product was purified by column chromatography using dichloromethane/hexane (1:1) as eluent to afford 1-(2-chloro-6-hydroxyphenyl)ethanone (100 mg, 15% yield).
