Hydrochloric Acid → 4-Fluorosalicylic acid

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (51.6 g, 373 mmol) was dried by heating at 200° C. for 12 hours. This was treated with 3-fluorophenol (16.5 g, 147 mmol) in a sealed container which was then pressurized with carbon monoxide at 61.2 bar. The reaction was heated to 175° C. for 5 hours. Subsequently, the reaction mixture was dissolved in water, acidified with concentrated hydrochloric acid, and filtered. The solid was washed with water, then hexanes. The solid was then dissolved in EtOAc, dried over magnesium sulfate, and concentrated to give 12 g of solid. This crude solid was purified by flash chromatrography using CHCl3/MeOH/HOAc 98:1:1 to give 11 g of a white solid which was recrystallized from toluene to give 9.5 g of the product as needles.

Provenance & Evidence