Boron tribromide → 3-(5-(3-Carbazol-9-ylphenyl)-1,3,4-oxadiazol-2-yl)phenol

Participants

Reaction Steps

To a solution of 2-(3-carbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (3.0 g, 72 mmol) in dichloromethane (20.0 ml) was dropwise added BBr3 (30.0 ml, 1M in dichloromethane) at −78° C. (dry-ice/acetone) under nitrogen. After addition of BBr3 solution, the reaction was taken to room temperature and kept at room temperature for 6 h. The reaction mixture was poured into ice-water (100.0 ml). Dichloromethane was evaporated under reduced pressure. The white solid was collected by filtration. After drying under vacuum, product as white solid was obtained in 2.9 g (100%) yield. 1H NMR (400 MHz, acetone-d6, δ): 8.89 (s, br, 1H, OH), 8.41 (m, 1H), 8.34 (m, 1H), 8.26 (m, 2H), 7.92 (m, 2H), 7.66 (m, 2H), 7.53-7.41 (m, 5H), 7.33 (m, 2H), 7.10 (m, 1H). MS-EI (m/z): [M]+ calcd for C26H17N3O2, 403.1. found 403.1.

Provenance & Evidence