Synthesis
General method: To a 10 mL solution of (formylmethylene)triphenylphosphine (1.5 mmol) in solvent (CH2Cl2 or THF) was added slowly and dropwise to a 4 mL solution of o-bromobenzaldehyde (1.0 mmol) in solvent (CH2Cl2 or THF) at 0 °C under argon protection. The reaction mixture was warmed to 25 °C with continuous stirring until the reaction was complete, and the progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by column chromatography on silica gel (60-120 mesh), with a mixed solvent of petroleum ether/ethyl acetate as eluent, to finally obtain the target product (E)-3-(2-bromophenyl)acrolein.
References
[1] Tetrahedron Letters, 2011, vol. 52, # 31, p. 4051 - 4055
[2] Organic and Biomolecular Chemistry, 2014, vol. 12, # 43, p. 8588 - 8592
[3] Organic Letters, 2016, vol. 18, # 4, p. 752 - 755
[4] Chemistry - A European Journal, 2018, vol. 24, # 22, p. 5765 - 5769
