Styrene → HCID 68773456, compound

Participants

Reaction Conditions

Reaction Steps

A schlenk tube was charged with 4,4′-dibromobenzil (2.0 g, 5.4 mmol), K2CO3 (3.75 g, 27.2 mmol), Bu4NBr (1.75 g, 5.4 mmol), LiCl (0.23 g, 5.4 mmol), Pd(OAc)2 (0.12 g, 0.54 mmol), styrene (1.6 mL, 13.6 mmol), and 50 mL of dry DMF. The reaction mixture was heated at 100° C. for 14 h. The reaction mixture was allowed to cool down to room temperature and extracted with CH2Cl2. The organic phase was washed with H2O and dried over anhydrous MgSO4. The solvent was removed under reduced pressure. The crude product was purified by column chromatography (silica gel, dichloromethane:hexanes=1:2 (v/v), then dichloromethane:hexanes=1:1 (v/v)) to give a light yellow solid (1.56 g, 69.3%). 1H NMR (300 MHz, CDCl3, δ): 7.97 (d, J=8.3 Hz, 4H), 7.62 (d, J=8.8 Hz, 4H), 7.53 (d, J=6.8 Hz, 4H), 7.27-7.40 (m, 6H), 7.26 (d, J=16.6 Hz, 2H), 7.12 (d, J=16.6 Hz, 2H). 13C{1H} NMR (75 MHz, CDCl3, δ): 193.82, 143.82, 136.45, 132.63, 131.83, 130.48, 128.83, 128.60, 127.17, 126.96, 126.84. HRMS-FAB (m/z): [M+H]+ calcd for C30H23O2, 415.1698; found, 415.1699. Anal. Calcd for C30H22O2: C, 86.93; H, 5.35. Found: C, 86.90; H, 5.26.

Provenance & Evidence