反应详情

To a solution of 2-(4-carbazol-9-ylphenyl)-5-(3-methoxyphenyl)-1,3,4-oxadiazole (1.0 g, 2.40 mmol) in dichloromethane (10.0 ml) was dropwise added BBr3 (10.0 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 h. The reaction mixture was poured into ice-water (50.0 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 0.97 g (100%) yield. 1H NMR (400 MHz, acetone-d6, δ): 8.91 (s, 1H, OH), 8.48 (m, 2H), 8.24 (dt, J1=8.0 Hz, J2=1.2 Hz, 2H), 7.91 (m, 2H), 7.71 (t, J=1.2 Hz, 1H), 7.69 (t, J=1.6 Hz, 1H), 7.56 (d, J=0.8 Hz, 1H), 7.54 (t, J=0.8 Hz, 1H), 7.46 (m, 3H), 7.32 (m, 2H), 7.12 (m, 111), 3.93 (s, 3H, OCH3). 13C NMR (100 MHz, acetone-d6, δ): 165.43, 164.72, 158.87, 141.48, 141.12, 131.44, 129.41, 128.23, 127.17, 126.04, 124.56, 123.65, 121.43, 121.26, 119.88, 118.89, 114.18, 110.62. MS-EI (m/z): [M]+ calcd for C26H17N3O2, 403.1. found 403.1.

1. customat −78° C.
2. customwas taken to room temperature
3. customDichloromethane was evaporated under reduced pressure
4. filtrationThe white solid was collected by filtration
5. customAfter drying under vacuum
6. customproduct as white solid was obtained in 0.97 g (100%)
7. customyield