3-Fluoroaniline → 2-(3-Fluoro-anilino)-4-methoxybenzoic acid

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Reaction Steps

4-methoxy-2-chloro-benzoic acid (2.0 g), potassium carbonate (1.78 g), 3-fluoroaniline (6.7 mL) and Cu powder (100 mg) were combined and heated at 125 C for 1 h. The reaction was cooled and partitioned between saturated aqueous sodium carbonate and ethyl ether. The aqueous solution was extracted once with ether, then the combined organic solutions were washed with saturated aqueous sodium carbonate (2×). The combined aqueous solutions were acidified to pH 3.5 with conc HCl and extracted with EtOAc (4×). The combined organic solutions were dried (MgSO4) and concentrated. Flash chromatography (0 to 10% MeOH in CH2Cl2) provided a solid, which was recrystallized from CH2Cl2/hexanes to give 1.9 g of 2-(3-fluoro-anilino)-4-methoxybenzoic acid.

Provenance & Evidence