4-Fluorobenzaldehyde → Ethyl 3-(4-fluorophenyl)prop-2-enoate

Participants

Reaction Steps

4-Fluorobenzaldehyde (27.2 ml, 0.23 Mol) and carboethoxymethylenetriphenylphosphorane (88.38 g, 0.23 Mol) were disolved in toluene (500 ml), and the mixture was heated overnight at reflux. The reaction was stripped then purified by flash chromatography in 25% EtOAc/Hexanes yielded 44.55g of a crystalline solid as product. NMR (300 MHz, CDCl3) δ 7.65 (d, 1H, J=16 Hz); 7.60-7.40 (m, 2H); 7.08 (t, 2H, J=7 Hz); 6.35 (d, 1H, J=16 Hz); 4.26 (q, 2H, J=7 Hz); 1.34 (t, 3H, J=7 Hz).

Provenance & Evidence