4-Bromobenzophenone → HCID 66591017, compound

Participants

Reaction Steps

In a suspension of 4-bromobenzophenone (5 g, 19.2 mmol) in 50 mL of THF were added TiCl4 (2.14 mL, 19.2 mmol) and Zn dust (2.48 g, 38.4 mmol). After reflux for 20 h, the reaction mixture was cooled to room temperature and filtered. The solvent was evaporated under vacuum and the crude product was purified by a silica gel column using hexane as eluent. 1,2-Bis(4-bromophenyl)-1,2-diphenylethene (5) was obtained as white solid in 95% yield (4.3 g). 1H NMR (CDCl3, 300 MHz), δ (ppm): 7.27 7.19 (m, 4H), 7.15 7.09 (m, 6H), 6.98 (m, 4H), 6.90 6.86 (m, 4H). 13C NMR (CDCl3, 75 MHz), δ (TMS, ppm): 133.0, 131.3, 131.2, 131.0, 128.1, 127.9, 127.8, 127.0, 126.9. MS (TOF): m/e 489.9 (M+, calcd. 490.0).

Provenance & Evidence