Hydrochloric Acid → 5-Bromo-4-fluoro-2-iodobenzoic acid

Participants

Reaction Steps

Sulfuric acid (19.36 mL, 363 mmol) was added to a solution of 2-amino-5-bromo-4-fluorobenzoic acid (5.00 g, 21.37 mmol) in concentrated HCl (5.13 mL, 64.1 mmol) at 0° C. To this was added a solution of sodium nitrate (1.816 g, 21.37 mmol) in water (9 mL). The reaction was stirred for 40 minutes at 0° C. before potassium iodide (7.09 g, 42.7 mmol) in water (9.00 mL) was added dropwise. The solution was stirred at rt for 1 hour, at which point it had become a viscous oil. The mixture was poured into a mixture of ice water (250 mL) with EtOAc (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (3×100 mL). The combined organic extracts were washed with 1N HCl, 1 N aqueous sodium sulfite, and dried over sodium sulfate. The solution was filtered and concentrated in vacuo to give 5-bromo-4-fluoro-2-iodobenzoic acid.

Provenance & Evidence