1-(4-chlorophenoxy)propan-2-one

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-(4-Chloro-phenoxy)-propan-2-one (2.66 g) was added to a stirred solution of [4-(methylthio)phenyl]-hydrazine hydrochloride (2.5 g) in MeCN (15 ml)/HCl (0.5M, 15 ml) at RT. The reaction was stirred at 50° C. for 1 h. After cooling to room temperature, the reaction was partitioned between ethylacetate/water, the organics were separated, washed with aq sodium hydroxide (1 M), dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-20% ethylacetate/iso-hexane. The resulting hydrazone was dissolved in THF (80 ml). Sodium bicarbionate solid (1.04 g) was added followed by phosphorus trichloride (0.41 ml) dropwise, and the reaction stirred at RT for 2 h. Further phosphorus trichloride (1.20 ml) was added dropwise, and the reaction stirred at RT for 16 h. The reaction was quenched with water. The mixture was extracted with ethylacetate, the organics washed with aq. sodium hydrogencarbonate, brine, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 5-10% ethylacetate/iso-hexane. Yield 0.45 g. After cooling to room temperature the reaction was partitioned between ethylacetate/water the organics were separated washed with aq sodium hydroxide (1 M) dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with 5-20% ethylacetate/iso-hexane The resulting hydrazone was dissolved in THF (80 ml) Sodium bicarbionate solid (1.04 g) was added the reaction stirred at RT for 2 h Further phosphorus trichloride (1.20 ml) was added dropwise the reaction stirred at RT for 16 h The reaction was quenched with water The mixture was extracted with ethylacetate the organics washed with aq. sodium hydrogencarbonate, brine dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with 5-10% ethylacetate/iso-hexane

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of the compound from (i) (2.4 g) and 1-(4-Chloro-phenoxy)-propan-2-one (1.65 g) in MeCN (20 ml) and water (5 ml) was stirred for 16 h. The volatiles were removed in vacuo. AcOH (50 ml) was added and the reaction heated at 75° C. for 72 h. The volatiles were evaporated under reduced pressure and the residue was purified by chromatography on silica eluting with 5% ethylacetate/iso-hexane. Yield 0.34 g The volatiles were removed in vacuo AcOH (50 ml) was added The volatiles were evaporated under reduced pressure the residue was purified by chromatography on silica eluting with 5% ethylacetate/iso-hexane

反応条件: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of the compound from (i) (2.4 g) and 1-(4-Chloro-phenoxy)-propan-2-one (1.65 g) in MeCN (20 ml) and water (5 ml) was stirred for 16 h. The volatiles were removed in vacuo. AcOH (50 ml) was added and the reaction heated at 75° C. for 72 h. The volatiles were evaporated under reduced pressure and the residue was purified by chromatography on silica eluting with 5% ethylacetate/iso-hexane. Yield 0.34 g The volatiles were removed in vacuo AcOH (50 ml) was added The volatiles were evaporated under reduced pressure the residue was purified by chromatography on silica eluting with 5% ethylacetate/iso-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-(4-Chloro-phenoxy)-propan-2-one (2.05 g) was added to a stirred solution of (4-fluoro-phenyl)-hydrazine (1.4 g) in ethanol (30 ml) at RT. After 2 h, the solvent was removed under reduced pressure and the residue dissolved in DCM (30 ml). Phosphorus trichloride (1.06 ml) was added dropwise to the solution and after stirring at RT for 16 h the reaction was quenched with aq. sodium hydrogencarbonate solution. The mixture was extracted with DCM, the organics washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane. Yield 0.75 g the solvent was removed under reduced pressure the residue dissolved in DCM (30 ml) Phosphorus trichloride (1.06 ml) was added dropwise to the solution was quenched with aq. sodium hydrogencarbonate solution The mixture was extracted with DCM the organics washed with water dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 1-(4-Chloro-phenoxy)-propan-2-one (2.05 g) was added to a stirred solution of (4-fluoro-phenyl)-hydrazine (1.4 g) in ethanol (30 ml) at RT. After 2 h, the solvent was removed under reduced pressure and the residue dissolved in DCM (30 ml). Phosphorus trichloride (1.06 ml) was added dropwise to the solution and after stirring at RT for 16 h the reaction was quenched with aq. sodium hydrogencarbonate solution. The mixture was extracted with DCM, the organics washed with water, dried and evaporated under reduced pressure. The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane. Yield 0.75 g the solvent was removed under reduced pressure the residue dissolved in DCM (30 ml) Phosphorus trichloride (1.06 ml) was added dropwise to the solution was quenched with aq. sodium hydrogencarbonate solution The mixture was extracted with DCM the organics washed with water dried evaporated under reduced pressure The residue was purified by chromatography on silica eluting with 20% ethylacetate/iso-hexane

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 4-chlorophenol (2.6 g, 20 mmol), chloroacetone (2.8 g, 30 mmol) and potassium carbonate (3.45 g, 25 mmol) in acetone (100 ml) is heated at reflux for 3 hours. The precipitating inorganic salts are filtered off and the filtrate is evaporated to dryness to give the 1-(4-chlorophenoxy)-propan-2-one. is heated at reflux for 3 hours The precipitating inorganic salts are filtered off the filtrate is evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension of 4-chlorophenol (2.6 g, 20 mmol), chloroacetone (2.8 g, 30 mmol) and potassium carbonate (3.45 g, 25 mmol) in acetone (100 ml) is heated at reflux for 3 hours. The precipitating inorganic salts are filtered off and the filtrate is evaporated to dryness to give the 1-(4-chlorophenoxy)-propan-2-one. is heated at reflux for 3 hours The precipitating inorganic salts are filtered off the filtrate is evaporated to dryness

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-Chlorophenol (10 g), chloroacetone (10.8 g), anhydrous potassium carbonate (12.9 g) and potassium iodide (1.3 g) were added to acetone (100 ml) and heated under reflux for 6 hours. The reaction mixture was filtered and the filtrate was concentrated to obtain 4-chlorophenoxyacetone (14 g). heated under reflux for 6 hours The reaction mixture was filtered the filtrate was concentrated