Potassium Iodide → 4-Iodo-3-(trifluoromethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

4-Amino-3-trifluoromethyl benzoic acid (1.8 g, 8.8 mmol) is suspended in conc. HCl (30 mL). A solution of sodium nitrite (0.76 g, 11.0 mmol) in water (15 mL) is added dropwise at 0° C. The mixture is stirred at 0-10° C. for 30 min. A solution of potassium iodide (14.6 g, 88 mmol) in water (25 mL) is added dropwise. The mixture is stirred at room temperature for 1 h. The product is extracted with EtOAc (80 mL), washed with brine (80 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure to a residue. The residue is purified by flash chromatography using a gradient (EtOAc/Hexane) to afford the title compound (2.4 g, 86%) as a solid. LC-ES/MS m/e 339.3 (M+23), 315.0 (M−1).

Provenance & Evidence