Boron tribromide → 4-((5-Bromo-1,3,4-thiadiazol-2-yl)oxy)phenol

Participants

Reaction Conditions

Reaction Steps

A solution of Example 24A (1.63 g, 5.67 mmol) in CH2Cl2 (75 mL) was cooled to −78° C. and the resulting suspension was treated with BBr3 (22.67 mmol, 2.14 mL) drop wise over 2 minutes. The reaction was stirred at 25° C. for 2 hours and was poured into a 200 mL ice/water mixture. The resulting bilayer was stirred vigorously for 0.5 hours and a white precipitate formed. The solids were filtered, washed with water (1×20 mL) and dried in a vacuum oven to provide 1.35 g (87%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.79 (br. s, 1H) 7.27 (d, J=9.19 Hz, 2H) 6.84 (d, J=9.19 Hz, 2H); MS (DCI) m/z 275 (M+H)+.

Provenance & Evidence