4-bromo-2-(dimethylamino)benzaldehyde

反応条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 4-bromo-2-dimethylaminobenzaldehyde (250 mg, 1.10 mmol), sodium carbonate (140 mg, 1.32 mmol), and phenylboronic acid (210 mg, 1.65 mmol) in 2.2 mL of N,N-dimethylformamide/water (2:1) was added palladium acetate (13 mg, 58 μmol) under nitrogen. After being stirred at 100° C. overnight, the reaction mixture was filtered. The filtrate was diluted with ethyl acetate, and the solution was washed with saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20) to obtain the title compound as a yellow oil (226 mg, 91%). the reaction mixture was filtered The filtrate was diluted with ethyl acetate the solution was washed with saturated NaHCO3 aqueous solution, brine dried over MgSO4 After filtration the filtrate was concentrated in vacuo the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 80/20)

反応条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a suspension of 4-bromo-2-fluorobenzaldehyde (500 mg, 2.46 mmol) and potassium carbonate (340 mg, 2.46 mmol) in 5 mL of dry N,N-dimethylformamide was added dimethylamine/ethanol solution (0.67 mL, 5.6 M, 3.8 mmol) at room temperature. After being stirred at 110° C. overnight, the reaction mixture was diluted with ethyl acetate. The solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound as a yellow oil (458 mg, 81%). The solution was washed with water, saturated NaHCO3 aqueous solution, brine dried over MgSO4 After filtration the filtrate was concentrated in vacuo the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)