1,2-Dibromoethane → 1-[2-(2-Bromoethoxy)-1-(3-fluorophenyl)ethenyl]-3-fluorobenzene

Participants

Reaction Steps

bis(3-Fluorophenyl)acetaldehyde (4.82 g, 0.0208 mol) was dissolved in dichloromethane (50 ml) and tetra-n-butyl ammonium bromide (0.67 g, 0.00208 mol) was added. 12 N sodium hydroxide solution (50 ml) and 1,2-dibromoethane (17.9 ml, 0.208 mol) were introduced and the mixture was stirred vigorously at room temperature for 20 h. Dichloromethane (100 ml) and saturated brine (50 ml) were added, and the phases were separated. The aqueous phase was extracted further with dichloromethane (50 ml) and the combined dichloromethane extracts were washed with water (2 × 75 ml) and saturated brine (50 ml). Drying of the dichloromethane solution (Na2SO4) and evaporation provided the title compound as an oil (6.66 g, 95%), TLC rf 0.71 (SiO2 dichloromethane).

Provenance & Evidence