Water → HCID 68654780, compound

Participants

Reaction Steps

To a cold (5° C.) solution of {(4-bromophenyl)[3-(methyloxy)phenyl]methylidene}cycloheptane (192) (0.557 g, 1.5 mmol) in CH2Cl2 (50 mL) was added BBr3 (0.425 mL, 4.5 mmol) slowly. The reaction mixture was stirred between 5° C. and 20° C. for 4 h and then carefully poured into water (100 mL). The layers were separated and the aqueous layer was further extracted with CH2Cl2 (2×50 mL) and the combined organic layer dried (Na2SO4). Concentration and purification by flash column chromatography gave 0.44 g (82%) of compound 193 as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 7.41 (d, J=8.4 Hz, 2H), 7.17 (dd, J1=7.8 Hz, J2=7.8 Hz, 1H), 7.05 (d, J=8.4 Hz, 2H), 6.74 (br d, J=7.5 Hz, 1H), 6.69 and 6.67 (dd, J1=2.4 Hz, J2=8.1 Hz, 1H), 6.62 (app t, J=1.8 Hz), 4.71 (s, 1H), 2.32 (br, m, 4H), 1.59 (br s, 8H).

Provenance & Evidence