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

Participants

Reaction Steps

To a solution of 2-(3,5-dicarbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (0.95 g, 1.63 mmol) in dichloromethane (20.0 ml) was dropwise added BBr3 (7.0 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 5.5 h. The reaction mixture was poured into ice-water (70.0 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 0.92 g (98.9%) yield. 1H NMR (400 MHz, DMSO-d6, δ): 10.01 (s, br, 1H, OH), 8.46 (d, J=1.6 Hz, 2H), 8.28 (d, J=8.0 Hz, 4H), 8.17 (t, J=1.6 Hz, 111), 7.66 (d, J=8.0 Hz, 4H), 7.59 (d, J=8.0 Hz, 1H), 7.50 (m, 5H), 7.34 (m, 5H), 7.00 (dd, J1=8.4 Hz, J2=2.4 Hz, 1H). MS-EI (m/z): [M]+ calcd for C38H24N4O2, 568.2. found 568.2.

Provenance & Evidence