Hydrochloric Acid → 5-Fluoro-2-iodobenzoic acid

Participants

Reaction Conditions

Reaction Steps

The title compound was prepared from the following procedure described in Collection Czechoslov. Chem. Commun., vol. 40, p. 719 (1975). To an ice-cold mixture of 2-amino-5-fluorobenzoic acid (9.0 g, 58.0 mmol) and conc. hydrochloric acid (50 mL) was added dropwise a solution of sodium nitrite (4.42 g, 64.1 mmol) in water (10 mL). Subsequently, a solution of potassium iodide (14.5 g, 87.5 mmol) and conc. sulfuric acid (4 mL) in water (30 mL) was added at the same temperature, and the mixture was heated to 100° C. and stirred for 2 hours. After the solution was cooled to room temperature, the mixture was poured into an aqueous solution of sodium thiosulfate, and organic matter was extracted with ethyl acetate. The extract was washed with saturated brine and water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give crude crystals. The crystals were collected by filtration, washed with hexane/diethylether, and air dried to give the title compound (6.33 g, 41% yield).

Provenance & Evidence