2'-氟-6'-羟基苯乙酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution (25 mL) of 1-(2-fluoro-6-hydroxyphenyl)ethanone (1.3 g) in N,N-dimethylformamide were added potassium carbonate (3.5 g) and 1-bromo-3-methylbutan-2-one (1.7 g) synthesized in Example A75(1) at room temperature, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was allowed to cool to room temperature, and filtered through celite. Water was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (15 mL) again, 1,8-diazabicyclo[5.4.0]undec-7-ene (1.3 mL) was added to the mixture, and the mixture was stirred at 110° C. for 1 hr with heating. After cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid, and the mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the precipitated compound was recrystallized from diisopropyl ether-hexane to give the title object compound (1.4 g, 77%) as a colorless solid. synthesized in Example A75(1) at room temperature to cool to room temperature filtered through celite Water was added to the filtrate the mixture was extracted with diethyl ether The extract was washed with saturated brine dried over magnesium sulfate concentrated under reduced pressure The obtained residue was dissolved in N,N-dimethylformamide (15 mL) again 1,8-diazabicyclo[5.4.0]undec-7-ene (1.3 mL) was added to the mixture the mixture was stirred at 110° C. for 1 hr with heating After cooling to room temperature the reaction mixture was quenched with 1N hydrochloric acid the mixture was extracted with diethyl ether The extract was concentrated under reduced pressure the precipitated compound was recrystallized from diisopropyl ether-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution (50 mL) of 1-(2-fluoro-6-hydroxyphenyl)ethanone (2.5 g) in N,N-dimethylformamide were added potassium carbonate (6.7 g) and 2-bromo-1-cyclohexylethanone (4.0 g) synthesized in Example A51(1) at room temperature, and the mixture was stirred at room temperature for 16 hr. The reaction mixture was allowed to cool to room temperature and filtered through celite. Water was added to the filtrate, and the mixture was extracted with diethyl ether. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The obtained residue was dissolved in N,N-dimethylformamide (50 mL) again, 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL) was added to the solution, and the mixture was stirred at 110° C. for 1 hr with heating. After cooling to room temperature, the reaction mixture was quenched with 1N hydrochloric acid, and the reaction mixture was extracted with diethyl ether. The extract was concentrated under reduced pressure, and the precipitated compound was recrystallized from diisopropyl ether-hexane to give the title object compound (2.6 g, 62%) as a colorless solid. synthesized in Example A51(1) at room temperature to cool to room temperature filtered through celite Water was added to the filtrate the mixture was extracted with diethyl ether The extract was washed with saturated brine dried over magnesium sulfate concentrated under reduced pressure The obtained residue was dissolved in N,N-dimethylformamide (50 mL) again 1,8-diazabicyclo[5.4.0]undec-7-ene (2.6 mL) was added to the solution the mixture was stirred at 110° C. for 1 hr with heating After cooling to room temperature the reaction mixture was quenched with 1N hydrochloric acid the reaction mixture was extracted with diethyl ether The extract was concentrated under reduced pressure the precipitated compound was recrystallized from diisopropyl ether-hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1-(2-Fluoro-6-hydroxy-phenyl)-ethanone (2.5 g, 16.22 mmol) (available from Apollo Scientific) was dissolved in anhydrous DMF (20 mL.) Dimethylthiocarbamoyl chloride (2.2 g, 17.84 mmol) and DABCO (2.0 g, 17.84 mmol) were added sequentially in one portion. The reaction was permitted to stir overnight at ambient temperature. The reaction was quenched by pouring it into a mixture of 1N HCl-ice. The oily residue was extracted with dichloromethane and dried over sodium sulfate. The crude residue was purified by SGC (20% ethyl acetate in hexanes) to provide the title compound (2.93 g.) 1H NMR (200 MHz, CDCl3): δ (ppm)=7.407 (dd, 1H), 7.026 (t, 1H), 6.876 (d, 1H), 3.404 (s, 3H), 3.341 (sd, 3H), 2.58 (d, 3H). were added sequentially in one portion The reaction was quenched by pouring it into a mixture of 1N HCl-ice The oily residue was extracted with dichloromethane dried over sodium sulfate The crude residue was purified by SGC (20% ethyl acetate in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4 is prepared from 2-fluoro-6-hydroxyacetophenone (see Example 6) and benzoyl chloride by the procedure of Example 1. The material is purified by flash chromatography (eluting with 25% ethyl acetate in hexane), yielding 4 with a melting point of 144°-145° C. The material is purified by flash chromatography (eluting with 25% ethyl acetate in hexane) yielding 4 with a melting point of 144°-145° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1-(2-Fluoro-6-hydroxy-phenyl)-ethanone (2.5 g, 16.22 mmol) (available from Apollo Scientific) was dissolved in anhydrous DMF (20 mL.) Dimethylthiocarbamoyl chloride (2.2 g, 17.84 mmol) and DABCO (2.0 g, 17.84 mmol) were added sequentially in one portion. The reaction was permitted to stir overnight at ambient temperature. The reaction was quenched by pouring it into a mixture of 1N HCl-ice. The oily residue was extracted with dichloromethane and dried over sodium sulfate. The crude residue was purified by SGC (20% ethyl acetate in hexanes) to provide the title compound (2.93 g.) 1H NMR (200 MHz, CDCl3): δ (ppm)=7.407 (dd, 1H), 7.026 (t, 1H), 6.876 (d, 1H), 3.404 (s, 3H), 3.341 (sd, 3H), 2.58 (d, 3H). were added sequentially in one portion The reaction was quenched by pouring it into a mixture of 1N HCl-ice The oily residue was extracted with dichloromethane dried over sodium sulfate The crude residue was purified by SGC (20% ethyl acetate in hexanes)