Trifluoromethanesulfonic acid → 1-Chloro-2,5-difluoro-4-iodobenzene
Reaction equation
FC(F)(F)S(O)(=O)=O.[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[F:17].[I:18]N1C(=O)CCC1=O>>[Cl:9][C:10]1[CH:15]=[C:14]([F:16])[C:13]([I:18])=[CH:12][C:11]=1[F:17]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
Trifluoromethanesulfonic acid (9.9 mL, 110 mmol) was added to 2-chloro-1,4-difluorobenzene (2.2 g, 15 mmol) at room temperature and then cooled to 0° C. N-Iodosuccinimide (3.16 g, 14.1 mmol) was then added in multiple portions. After 10 minutes, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The reaction mixture was poured over ice-water and extracted with hexane. The organic layer was washed with saturated Na2SO4, dried and concentrated. The crude product was purified by silica gel chromatography (100% hexanes) to give 1-chloro-2,5-difluoro-4-iodobenzene (3.0 g, 74%). 1H NMR (400 MHz, CDCl3) δ 7.52 (dd, J=5.4, 7.8, 1H), 7.17-7.08 (m, 1H).