(E)-1,2-bis(4-bromophenyl)-1,2-diphenylethene synthesis

Yield: 65%

Reaction Conditions:

with titanium tetrachloride;zinc in tetrahydrofuran for 12.5 h;Inert atmosphere;Reflux;

Steps:

1,2-Bis(4-bromophenyl)-1,2-diphenylethene (TPEDBr).
Zincdust (2.25 g, 34.7 mmol) and 4-bromobenzophenone (3 g, 11.5 mmol)were charged into a triple-neck round-bottom flask of 250 mL volume containing anhydrous THF (50 mL) at 0 °C. Subsequently, titanium tetrachloride (1.89 mL, 17.3 mmol) was added dropwise under argonflow. Following removal from the ice bath, the reaction mixture was stirred at room temperature for 30 min and there after refluxed for 12 h.Subsequently, the mixture was cooled to room temperature, quenched using a 10% aqueous solution of potassium carbonate, and extracted three times using methylene chloride. The purification of the crude product by column chromatography on silica gel using a mixture ofhexane and ethyl acetate (3:1 v/v) as the eluent yielded a light-yellow solid (yield = 65%). 1H NMR (400 MHz, CDCl3):δ = 7.27-7.21 (m,4H, Ar H), 7.14-7.10 (m, 6H, Ar H), 7.04-6.94 (m, 4H; Ar H), 6.86-6.90(m, 4H; Ar H) ppm. 13C NMR (101 MHz, CDCl3): = δ142.90, 142.81,142.37, 142.27, 140.27, 132.96, 132.88, 132.86, 131.28, 131.20,131.18, 131.09, 130.89, 130.83, 128.01, 127.86, 127.81, 127.76,127.66, 126.93, 126.82, 120.78, 120.65.

References:

Augustine, Rimesh;Kalva, Nagendra;Kim, Il;Lee, Min Woong;Lee, Soo Jeong;Tran, Chinh Hoang [Dyes and Pigments,2021,vol. 194]