Boron tribromide → (E)-2-(4-fluoro-2-methylphenyl)-3-(4-(2-(5-methyl-1,3,4-oxadiazol-2-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol

Participants

Reaction Steps

To a 30 mL screw cap vial, (E)-2-(4-((2-(4-fluoro-2-methylphenyl)-6-methoxybenzo[b]thiophen-3-yl)oxy)styryl)-5-methyl-1,3,4-oxadiazole (12 mg, 0.025 mmol) was dissolved in DCM (0.5 mL). The vial was charged with BBr3 (1.0 M in hexanes, 0.076 ml, 0.076 mmol) and the reaction mixture was stirred for 1 b at room temperature. The reaction mixture was quenched with 2 mL MeOH and stirred for 10 min. The mixture was concentrated onto silica gel and the crude material was purified by reverse phase HPLC (acidic condition, 0.1% TFA in 30-100% CH3CN/H2O) to afford (E)-2-(4-fluoro-2-methylphenyl)-3-(4-(2-(5-methyl-1,3,4-oxadiazol-2-yl)vinyl)phenoxy)benzo[b]thiophen-6-ol (3 mg, 6.54 μmol, 26% yield) as a yellow solid. 1H NMR (400 MHz, CD3OD) δ ppm=2.26 (s, 3 H), 2.45 (s, 3 H), 6.73-6.86 (m, 5 H), 6.88 (dd, J=9.85, 2.78 Hz, 1 H), 7.08-7.30 (m, 3 H), 7.34-7.45 (m, 3 H), LC/MS (m/z, MH+): 459.4.

Provenance & Evidence