5-bromo-2-fluoro-N,N-dimethylbenzamide

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: A suspension of 2-fluoro-5-bromobenzoic acid (680 mg, 3.10 mmol) in methylene chloride (20 ml) was treated with oxalyl chloride (0.35 ml, 4.04 mmol), followed by four drops of N,N-dimethylformamide. The resulting clear solution was stirred for about three hours. The solvents were removed in vacuo and the residue was redissolved in methylene chloride and treated with dimethylamine (4.6 ml, 9.3 mmol). Stirring was continued for 18 hours. The reaction mixture was diluted with methylene chloride, and washed with saturated sodium bicarbonate and brine. The organic fraciton was dried over sodium sulfate, and the solvents were removed in vacuo. The desired title product was further purified by liquid chromatography. The solvents were removed in vacuo the residue was redissolved in methylene chloride Stirring was continued for 18 hours washed with saturated sodium bicarbonate and brine The organic fraciton was dried over sodium sulfate the solvents were removed in vacuo The desired title product was further purified by liquid chromatography

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

実験手順: 5-Bromo-2-fluorobenzoic acid (500 mg, 2.23 mmol) was dissolved in DMF (5.0 mL), and dimethylamine hydrochloride (223 mg, 2.72 mmol), WSC.HCl (511 mg, 2.66 mmol), HOBt.H2O (410 mg, 2.68 mmol), and potassium carbonate (367 mg, 2.66 mmol) were added thereto, and the mixture was stirred at room temperature for 3 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50) to give 5-bromo-2-fluoro-N,N-dimethylbenzamide (550 mg, 2.23 mmol, yield: 99%). the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50)

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

実験手順: 5-Bromo-2-fluorobenzoic acid (500 mg, 2.23 mmol) was dissolved in DMF (5.0 mL), and dimethylamine hydrochloride (223 mg, 2.72 mmol), WSC.HCl (511 mg, 2.66 mmol), HOBt.H2O (410 mg, 2.68 mmol), and potassium carbonate (367 mg, 2.66 mmol) were added thereto, and the mixture was stirred at room temperature for 3 hours. To the mixture, an aqueous sodium hydrogen carbonate solution was added, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50) to give 5-bromo-2-fluoro-N,N-dimethylbenzamide (550 mg, 2.23 mmol, yield: 99%). the mixture was extracted with ethyl acetate The organic layer was washed with saturated brine dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/50)

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

実験手順: A suspension of 2-fluoro-5-bromobenzoic acid (680 mg, 3.10 mmol) in methylene chloride (20 ml) was treated with oxalyl chloride (0.35 ml, 4.04 mmol), followed by four drops of N,N-dimethylformamide. The resulting clear solution was stirred for about three hours. The solvents were removed in vacuo and the residue was redissolved in methylene chloride and treated with dimethylamine (4.6 ml, 9.3 mmol). Stirring was continued for 18 hours. The reaction mixture was diluted with methylene chloride, and washed with saturated sodium bicarbonate and brine. The organic fraciton was dried over sodium sulfate, and the solvents were removed in vacuo. The desired title product was further purified by liquid chromatography. The solvents were removed in vacuo the residue was redissolved in methylene chloride Stirring was continued for 18 hours washed with saturated sodium bicarbonate and brine The organic fraciton was dried over sodium sulfate the solvents were removed in vacuo The desired title product was further purified by liquid chromatography