3-Bromobenzaldehyde → 2-{[1-(3-Bromo-phenyl)-methylidene]-amino}-5-fluoro-benzoic acid methyl ester

Participants

Reaction Steps

A mixture of 2-amino-5-fluoro-benzoic acid methyl ester (15 g, 89 mmol) and 3-bromo-benzaldehyde (16.4 g, 89 mmol) in ethanol (200 mL) was heated to reflux for 2 hours. Then the reaction mixture cooled to room temperature. The solvent was removed in vacuo and the residue was washed with ether to afford 2-{[1-(3-bromo-phenyl)-methylidene]-amino}-5-fluoro-benzoic acid methyl ester (15.3 g, 52%) as a white solid: LC/MS m/e calcd for C15H11BrFNO2 M+: 336.2, observed: 336.2.

Provenance & Evidence