Acetic Acid → Methyl 3-(((4-fluorophenyl)amino)methyl)benzoate

Participants

Reaction Steps

To a stirred solution of methyl 3-formylbenzoate (0.5 g, 3.046 mmol) in anhydrous DCM (15 mL) was added 4-fluoroaniline (0.303 mL, 3.198 mmol) followed by glacial acetic acid (0.174 mL, 3.046 mmol). The reaction was stirred at room temperature for 64 hours. Sodium triacetoxyborohydride (1.614 g, 7.615 mmol) was added, and the reaction was stirred at room temperature for 2 hours. Water was added to quench the reaction and the mixture was diluted with DCM. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo to afford the title compound as a red oil (0.805 g, quantitative yield).

Provenance & Evidence