Water → HCID 11312729, compound

Participants

Reaction Steps

To a cold (5° C.) solution of 4-{cycloheptylidene[4-(methyloxy)phenyl]methyl}benzonitrile (207) (0.300 g, 0.94 mmol) in CH2Cl2 (20 mL) was added BBr3 (0.358 mL, 3.79 mL). The resultant reaction mixture was stirred between 5° C. and 20° C. for 3 h. Reaction mixture was poured into water (125 mL) and then extracted with CH2Cl2 (3×50 mL). The combined organic layer was dried and concentrated under reduced pressure to afford the crude product. The product was purified by flash column chromatography to give 0.245 g (86%) of compound 208 as a white solid. mp 110-111° C. IR (film): 3391, 2921, 2852, 2229, 1609, 1509, 1213, 829, 731 cm−1. 1H NMR (300 MHz, CDCl3): δ 7.57 (d, J=8.4 Hz, 2H), 7.27 (d, J=8.4 Hz, 2H), 7.00 (d, J=8.7 Hz, 2H), 6.79 (d, J=8.4 Hz, 2H), 4.97 (br s, 1H), 2.35 (br s, 2H), 2.29 (br s, 2H), 1.60 (br s, 8H). LCMS (ESI): m/z 302 (M−H)−. Anal. Calcd for C21H21NO, C, 83.13; H, 6.98; N, 4.62; Found: C, 83.13; H, 6.96; N, 4.62.

Provenance & Evidence