4-Bromo-2-fluorobenzaldehyde → 2-Fluoro-4-phenylbenzaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 4-bromo-2-fluorobenzaldehyde (0.15 g, 0.74 mmol), tributyl(phenyl)stannane (0.27 mL, 0.81 mmol) and Pd(PPh3)4 (0.043 g, 0.037 mmol) in PhCH3 (2.5 mL) was heated in a sealed reaction tube to 110° C. for 12 h. Additional tributyl(phenyl)stannane (0.20 mL, 0.61 mmol) and Pd(PPh3)4 (0.043 g, 0.037 mmol) were added and the solution was further heated to 110° C. for 2 h. The solvent was removed in vacuo. The residue was purified via column chromatography (SiO2, 5:1 hexanes/EtOAc) to provide 0.23 g (>100% yield) of 3-fluorobiphenyl-4-carbaldehyde, which was used without further purification: MS (EI) for C13H9OF: 201 (MH+).

Provenance & Evidence