Sodium Sulfite → 3-Fluoro-4-iodo-2-methylaniline

Temperature

70 °C

Iodine monochloride (0.5 ml) was added to a solution of 3-fluoro-2-methylaniline (1.25 g) in glacial acetic acid (15 ml). The mixture was stirred for two hours at 70° C. The mixture was allowed to cool to ambient temperature and saturated sodium sulphite solution (50 ml) was added. The solution was extracted with EtOAc (2×100 ml), and the extracts were combined, washed with saturated sodium bicarbonate solution (100 ml) and dried. The volatile material was removed by evaporation and the residue was purified by chromatography on silica gel, eluted with 0-10% EtOAc in hexane to give the title compound (1.53 g) as a solid. NMR: 1.98 (s, 3H), 5.32 (s, 2H), 6.30 (d, 1H), 7.20 (t, 1H); m/z: 250.

1. temperatureto cool to ambient temperature
2. extractionThe solution was extracted with EtOAc (2×100 ml)
3. washwashed with saturated sodium bicarbonate solution (100 ml)
4. customdried
5. customThe volatile material was removed by evaporation
6. customthe residue was purified by chromatography on silica gel
7. washeluted with 0-10% EtOAc in hexane

ORD record

ord-490cd3818226460c95cebe90dcf0ec5c

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06689909B1