Potassium Carbonate → 5-Cyclopropyl-4-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxymethyl]-3-(2-trifluoromethoxy-phenyl)-isoxazole

Participants

Reaction Conditions

Reaction Steps

To a 5-L 3-neck round bottom flask with a mechanical stirrer, thermocouple, reflux condenser, and drying tube is added 4-bromomethyl-5-cyclopropyl-3-(2-trifluoromethoxy-phenyl)-isoxazole (221.7 g, 0.612 mol, 1.05 eq), acetonitrile (2 L), 3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (136.5 g, 0.583 mol, 1 eq) and potassium carbonate (241.8 g, 1.749 mol, 3 eq). The reaction mixture is heated to reflux and stirred at this temperature for 1 hour. Upon completion of the reaction, as evidenced by thin layer chromatography, the reaction mixture is cooled to 0-20° C. The reaction mixture is filtered and the filter cake is washed with acetonitrile (2×100 mL). The reaction mixture is concentrated under reduced pressure to a solid which is co-evaporated with 1,4-dioxane (500 mL). The title compound is used without further purification. 1H NMR (DMSO-d6, 300 MHz): δ 7.7-7.5 (m, 5H), 6.61 (m, 2H), 4.90 (s, 2H), 2.39 (m, 1H), 2.36 (s, 3H), 1.24 (s, 12H), 1.10 (m, 4H).

Provenance & Evidence