N-Iodosuccinimide → 4-Bromo-5-fluoro-2-iodoaniline
Reaction equation
[I:1]N1C(=O)CCC1=O.[Br:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[F:17]>CC(O)=O.C1(C)C=CC=CC=1>[Br:9][C:10]1[C:11]([F:17])=[CH:12][C:13]([NH2:14])=[C:15]([I:1])[CH:16]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
N-iodosuccinimide (2.90 ml, 28.9 mmol) was added to a solution of 4-bromo-3-fluoroaniline (5.00 g, 26.3 mmol) in AcOH (52.6 ml). The reaction was maintained at ambient temperature for 1.5 h, then diluted with 20 mL toluene and concentrated. The residue was dissolved in EtOAc and washed with 2 N aqueous NaOH. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (40-g Ultra SNAP column, 25-g silica gel loading column, 2-10% EtOAc/Heptane) to give 4-bromo-5-fluoro-2-iodoaniline (7.23 g, 22.89 mmol, 87% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ 7.74-7.78 (m, 1H), 6.53-6.57 (m, 1H). m/z (ESI) 315.9 (M+H)+.