N-Iodosuccinimide → 875306-75-5

Participants

Reaction Steps

6.16 g of N-iodosuccinimide (27 mmol) were slowly added to a solution of 4.9 g of 3-fluoro-4-(trifluoromethyl)-aniline (27 mmol) in 20 ml acetic acid. After the reaction mixture had been stirred for 1.5 h at rt it was diluted with ether and washed with a 2 molar solution of Na2S2O3 and with brine. The ether layer was then dried with magnesium sulfate, filtered and the solvent was evaporated. 5-Fluoro-2-iodo-4-trifluoromethyl-aniline was isolated from the remaining residue by chromatography (silica gel; cyclohexane/EtOAc 4:1). This yielded 3.27 g (39%) of 5-fluoro-2-iodo-4-trifluoromethyl-aniline as a dark red liquid. 1H-NMR (CDCl3, 300 MHz): δ 4.52 (br s, 2H), 6.49 (d, J=12 Hz, 1H), 7.79 (d, J=8 Hz, 1H).

Provenance & Evidence