S(=O)(=O)(O)O.Br.N[C:8]1[C:16]([F:17])=[CH:15][C:14]([Br:18])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11].Cl.N([O-])=O.[Na+].[I-:24].[K+]>O>[Br:18][C:14]1[CH:15]=[C:16]([F:17])[C:8]([I:24])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11]
Sulfuric acid (47.0 mL, 882 mmol) was added to a mixture of 2-amino-5-bromo-3-fluorobenzoic acid hydrobromide (16.34 g, 51.9 mmol) and HCl (12.45 mL, 156 mmol) at 0° C. The resulting slurry was stirred at 0° C. and sodium nitrite (3.58 g, 51.9 mmol) in water (20 mL) was added dropwise over 10 minutes. The reaction was stirred 40 minutes at 0° C. before a solution of potassium iodide (17.23 g, 104 mmol) in water (20.00 mL) was added dropwise. The solution was stirred allowed to warm to RT, leading to the formation of a viscous mixture. After 1 hour at ambient temperature, the reaction was poured into ice water (500 mL) and the resulting precipitate was filtered. The black solid was washed with well water to give a dark brown solid which was dried in a vacuum oven at 50° C. for 12 hours to afford 5-bromo-3-fluoro-2-iodobenzoic acid as an orange/tan solid. MS m/z=344.8 [M+H].
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