Toluene → 1-Bromo-4-chloro-5-(4-ethylbenzyl)-2-vinylbenzene

Participants

Reaction Steps

To a suspension of Ph3PCH3I (3.151 g, 7.8 mmol) in 22 mL of dry toluene, was added dropwise with KN(TMS)2 (15.64 mL, 7.8 mmol, 0.5 M in toluene) under argon. After it was stirred for 1 h, a solution of 2-bromo-5-chloro-4-(4-ethylbenzyl)benzaldehyde (1.76 g, 5.2 mmol) in 17 mL of toluene was added. This reaction mixture was stirred at room temperature and monitored by TLC (PE, Rf=0.8). After being stirred for 4 h, the reaction mixture was quenched by addition of 5 mL of saturated NaHCO3. The organic layer was washed 2× with H2O, 2× with brine, dried over anhydrous Na2SO4. Concentration under reduced pressure provided the crude product, which was purified by column chromatography on silica gel (PE), to give the title compound as a colorless oil. Yield: 3.0 g (96%). 1H NMR (CDCl3, 300 MHz) δ 7.54 (s, 1H), 7.33 (s, 1H), 7.14 (d, J=2.1 Hz, 1H), 7.12 (d, J=2.4 Hz, 1H), 7.10 (d, J=2.1 Hz, 1H), 7.09 (d, J=2.4 Hz, 1H), 6.92 (dd, J=11.0, 17.6 Hz, 1H), 5.68 (dd, J=17.6, 0.9 Hz, 1H), 5.37 (dd, J=11.0, 0.9 Hz, 1H), 4.02 (s, 2H), 2.63 (q, J=7.6 Hz, 2H), 1.23 (t, J=7.6 Hz, 3H).

Provenance & Evidence