1-(4-bromophenyl)-1-phenylethylene

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 4-bromoacetophenone (10.0 g, 50.2 mmol) in 130 mL of dry diethyl ether was added over 1.5 hours to a solution of phenyllithium (30.7 mL of 1.8 M a solution in dibutyl ether, 55.2 mmol) in 70 mL of dry diethyl ether at room temperature under an inert atmosphere. The reaction mixture was stirred while heating to reflux for 3 hours and then was examined by [C-MS which showed complete consumption of starting material. The reaction was quenched with water (500 mL), until gas evolution ceased, and 1 N HCL (31 mL). The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The crude product was used without any further purification. A solution of the crude (1-(4-bromo-phenyl)-1-phenyl-ethanol) and a catalytic amount of p-toluenesulfonic acid in toluene (100 mL) was heated at 120° C. for 16 h in a flask equipped with a Dean-Stark apparatus. The reaction mixture was examined by LC-MS which showed complete consumption of starting material. Solvent was evaporated under reduced pressure and the crude was purified by flash chromatography eluting with cyclohexane/ethyl acetate (100:0 to 98:2) giving 11 g of the title compound as a colorless oil (Yield: 84%) while heating to reflux for 3 hours consumption of starting material The reaction was quenched with water (500 mL), until gas evolution The organic layer was separated dried over sodium sulfate concentrated under reduced pressure The crude product was used without any further purification equipped with a Dean-Stark apparatus consumption of starting material Solvent was evaporated under reduced pressure the crude was purified by flash chromatography eluting with cyclohexane/ethyl acetate (100:0 to 98:2)