Boron tribromide → HCID 58156773, compound

Participants

Reaction Steps

Methyl 4-[5-(3-cyanophenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]benzoate (0.60 g, 1.87 mmol) is then treated with boron tribromide (1M in dichloromethane, 5.6 mL, 5.6 mmol) in dichloromethane (20 mL) at room temperature overnight. The volatiles are removed in vacuum and the residue is treated with water. The crude product is separated by column chromatography (silica gel, 1:9 methanol-dichloromethane) to furnish the desired product, 4-[5-(3-cyanophenyl)-2-oxo-1,3,4-oxadiazol-3(2H)-yl]benzoic acid (0.46 g, 81%). m.p. 294-295° C. (decomp.). 1H NMR (CDCl3, 300 MHz) δ (ppm) 7.47 (t, 1H), 7.77 (d, 2H), 7.88-8.00 (m, 4H). (ES+) m/z: 307.

Provenance & Evidence