N-(4-bromo-2-chlorophenyl)-3-chloropropanamide

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hr. After cooling to room temperature, the mixture was treated with ice-water slowly and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27% yield) as a white solid. A flame-dried 500-mL flask equipped with a magnetic stirring bar After cooling to room temperature extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhy Na2SO4, filtered concentrated in vacuo The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hr. After cooling to room temperature, the mixture was treated with ice-water slowly and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27% yield) as a white solid. A flame-dried 500-mL flask equipped with a magnetic stirring bar After cooling to room temperature extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhy Na2SO4, filtered concentrated in vacuo The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

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

実験手順: To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15° C. After stirring at room temperature for 1 hr, the mixture was washed with water and then 2 N aq. hydrochloric acid. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to afford the title compound (10.9 g, 90% yield) as a white solid. the mixture was washed with water The organic layer was dried over anhy Na2SO4, filtered concentrated in vacuo

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hour. After cooling to room temperature, the mixture was treated slowly with ice-water and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27%) as a white solid. A flame-dried 500-mL flask equipped with a magnetic stirring bar After cooling to room temperature extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhydrous Na2SO4 filtered concentrated in vacuo The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

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

実験手順: To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15° C. After stirring at room temperature for 1 hour, the mixture was washed with water and then hydrochloric acid (2 N, aqueous). The organic layer was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to afford title compound (10.9 g, yield: 90%) as a white solid. the mixture was washed with water The organic layer was dried over anhydrous Na2SO4 filtered concentrated in vacuo

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A flame-dried 500-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-2-chloro-phenyl)-3-chloro-propionamide (29.7 g, 0.1 mol) and aluminium chloride (53.3 g, 0.4 mol). In a pre-heated oil bath, the flask was heated at 140° C. for 1 hr. After cooling to room temperature, the mixture was treated with ice-water slowly and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane) to afford the title compound (7.0 g, 27% yield) as a white solid. A flame-dried 500-mL flask equipped with a magnetic stirring bar After cooling to room temperature extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhy Na2SO4, filtered concentrated in vacuo The resulting residue was then purified by flash chromatography (silica gel, 30% ethyl acetate in hexane)

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

実験手順: To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15° C. After stirring at room temperature for 1 hr, the mixture was washed with water and then 2 N aq. hydrochloric acid. The organic layer was dried over anhy. Na2SO4, filtered, and concentrated in vacuo to afford the title compound (10.9 g, 90% yield) as a white solid. the mixture was washed with water The organic layer was dried over anhy Na2SO4, filtered concentrated in vacuo