N-Iodosuccinimide → 5-Fluoro-2-iodo-4-(trifluoromethyl)aniline

Reaktionsgleichung

[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][C:16]=1[C:17]([F:20])([F:19])[F:18])[NH2:13]>C(O)(=O)C.CCOCC>[F:9][C:10]1[C:16]([C:17]([F:18])([F:19])[F:20])=[CH:15][C:14]([I:1])=[C:12]([CH:11]=1)[NH2:13]

Komponenten

Versuchsvorschrift

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).