3-Fluorobenzaldehyde → Ethyl 3-(3-fluorophenyl)prop-2-enoate

Participants

Reaction Steps

To a solution of 3-fluorobenzaldehyde 3-1 (18.16 g, 146 mmol) in dichloromethane (500 mL) was added ethyl (triphenylphosphoranylidene)acetate (61.2 g; 176 mmol) and the resulting solution was stirred at room temperature for 18 hr. After evaporation of the solvent, the residue was swirled with ether/hexane and filtered. The filtrate was concentrated and then purified on a plug of silica gel eluting with hexane/EtOAc 9:1. Removal of the solvent afforded the title compound 3-2 as an oil (~95% trans) which was used without further purification in the next step. 1H NMR (300 MHz, CDCl3) δ 1.36 (3H, t), 4.28 (2H, q), 6.43 (1H, d), 7.08 (1H, m), 7.2-7.4 (3H, m), 7.64 (1H, d).

Provenance & Evidence