Water → 2-Anilino-4-fluorobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluoro-2-bromo-benzoic acid (25 g, 114 mmol), aniline (12.5 mL, 137 mmol), potassium carbonate (17.4 g, 126 mmol), copper powder (725 mg, 11.4 mmol), and copper (I) iodide (1.09 g, 5.71 mmol) in 2-ethoxyethanol (70 mL) was stirred at 138° C. for 70 hr. under an argon atmosphere. The reaction mixture was cooled to room temperature, then water (60 mL) was added. The mixture was filtered through celite. The filtrate was adjusted to pH<2, then an additional 200 mL of water was added. The mixture was allowed to stir for 1 hr. The precipitated solids were collected via filtrated. The solids were taken up into 5% sodium carbonate solution, then filtered. The product was dried under vacuum overnight at 85° C.

Provenance & Evidence