Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → methyl (E)-3-(4-chloro-2-nitrophenyl)acrylate

Participants

Reaction Steps

4-Chloro-2-nitrobenzaldehyde (5 g, 0.027M) was dissolved in toluene (150 ml) with methyl (triphenylphosphoranylidene) acetate (9.91 g, 1.1 molar equivalents) and heated under reflux for 1h. The reaction mixture was concentrated under vacuum and the residue was purified by chromatography on silica gel using dichloromethane as eluent to give the required compound (6.4 g, 98%) as a solid. δ(360MHz, CDCl3) 3.83 (3H, s, CH3), 6.36 (1H, d, J=15.9Hz, CHA =CHB), 7.58 (1H, d, J=8.4Hz, 6H), 7.63 (1H, dd, J=8.4 and 2.0Hz, 5-H), 8.04 (1H, d, J=2.0Hz, 3-H), 8.05 (1H, d, J=8.4Hz, CHA =CHB); MS (EI) m/e 241 [M+ ].

Provenance & Evidence