Potassium Iodide → 3-Fluoro-2-iodobenzoic acid

Participants

Reaction Conditions

Reaction Steps

Sodium nitrite (6.7 g, 97 mmol) in water (25 mL) was added to a solution of 2-amino-3-fluorobenzoic acid (10.0 g, 64 mmol) in DMSO (25 mL) and 30% H2SO4 (75 mL) at 0° C. The mixture was stirred for 1 hour at 0° C. and then potassium iodide (27 g, 161 mmol) was added dropwise as a solution in water (25 mL). The ice bath was removed and the mixture was stirred at room temperature for 4 hours, and then partitioned between EtOAc and 2M sodium sulfite. The layers were mixed, separated, and the organic layer was washed with 2M sodium sulfite once and brine once, dried over anhydrous MgSO4, and concentrated in vacuo to give 14.90 g of a yellow solid. MS m/e=265 (M−H)+.

Provenance & Evidence