39998-81-7

124700-40-9

The general procedure for the synthesis of 2-fluoro-4-iodobenzoic acid from 2-fluoro-4-iodotoluene was as follows: 13.39 g (84.74 mmol) of potassium permanganate was added to an aqueous suspension containing 5 g (21.18 mmol) of 2-fluoro-4-iodotoluene and 25.13 g (317.77 mmol) of pyridine. The reaction mixture was heated to 70 °C with continuous stirring. If the reaction was not complete, 3.34 g (21.18 mmol) of potassium permanganate was added to the reaction mixture at room temperature and the mixture was continued to be stirred at 70 °C for 6 hours. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and washed sequentially with water and ethyl acetate. After decantation, the aqueous phase was acidified with aqueous 6N HCl to pH=1. A white solid was first filtered and the aqueous phase was extracted three times with ethyl acetate. The combined organic phases were dried with MgSO4 and evaporated under reduced pressure to remove the solvent. The white solid obtained by initial filtration was combined with the solid obtained by ethyl acetate extraction to give 4.1 g of product in 73% yield. The product was confirmed by mass spectrometry with the molecular ion peak MH+ = 266.9 (C7H4FIO2).1H NMR (DMSO-d6, 400 MHz) data were as follows: δ 13.49 (broad peak, 1H); 7.88 (d, 1H); 7.78 (d, 1H); 7.65 (d, 1H).