Pyridine, hydrofluoride (1:1) → 2-Fluoro-3-iodo-4-methylbenzoic acid

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Reaction Steps

2-Amino-3-iodo-4-methylbenzoic acid (3.9 g, 14 mmol) was added slowly at 0° C. to HF-pyridine (30 mL). The mixture was stirred for 15 min and then sodium nitrite (1.5 g, 21 mmol) was added slowly at 0° C. The resulting mixture was stirred at 0° C. for 15 min and warmed up to RT for 15 min, then heated at 90° C. for 1.5 h. The mixture was cooled to 50° C., ice-water (100 mL) was added and the mixture was extracted with EtOAc (3×80 mL). The combined organic extracts were washed with brine (100 mL) and dried over sodium sulfate. The solvent was removed in vacuo to give the title compound (3.5 g, 89%). MS (M+H)+ 281.

Provenance & Evidence