Potassium Carbonate → 4-Bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde

Participants

Reaction Steps

To a mixture of 3-(3-bromoprop-1-ynyl)-5-phenyl-4-(trifluoromethyl)isoxazole (Preparation 62C, 0.219 g, 0.663 mmol) and 4-bromo-2-hydroxybenzaldehyde (0.133 g, 0.663 mmol) in dimethylformamide (2.0 mL) at room temperature was added potassium carbonate (0.115 g, 0.829 mmol). The reaction mixture was stirred at room temperature for 3 h, diluted with ethyl acetate (75 mL), washed with a 10% aqueous solution of lithium chloride (2×25 mL), and washed with brine (25 mL). The organic layer was collected, and the combined aqueous phases were extracted with ethyl acetate (2×25 mL). The combined organic layers were dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded a tan solid which was triturated with methanol with sonication to give 4-bromo-2-(3-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)prop-2-ynyloxy)benzaldehyde (0.223 g, 0.495 mmol, 75% yield) as a white solid. The product had an HPLC ret. time=3.28 min.−Column: Chromolith SpeedROD 4.6×50 mm (4 min.); Solvent A=10% MeOH, 90% H2O, 0.1% TFA; Solvent B=90% MeOH, 10% H2O, 0.1% TFA. LC/MS M+1=451.92. 1H NMR (500 MHz, CDCl3) δ ppm 5.12 (s, 2H), 7.28 (d, J=8.32 Hz, 1H), 7.34 (d, J=1.66 Hz, 1H), 7.51-7.55 (m, 2H), 7.56-7.61 (m, 1H), 7.72 (d, J=7.21 Hz, 2H), 7.75 (d, J=8.32 Hz, 1H), and 10.44 (s, 1H).

Provenance & Evidence