Potassium Iodide → 4-Iodophenylsulfur Pentafluoride

To a solution of 4-(pentafluorothio)aniline (15.0 g, 68.4 mmol) and ice (40.0 g) in hydrochloric acid (12M, 30 ml) was added a solution of sodium nitrite (5.0 g, 72.5 mmol) in water (120 ml) at 0° C. After stirring for 2 min, the mixture was added to potassium iodide (13.0 g, 78.3 mmol) in water (120 ml), ensuring the temperature did not rise above 10° C. The reaction mixture was stirred at 0° C. for 10 min and then at room temperature for 60 h. The mixture was extracted with diethyl ether (2×100 ml) and the combined extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (silica, 300 g), eluting with diethyl ether:cyclohexane [1:10]. The appropriate fractions were combined and concentrated to give the title compound (16.6 g).

1. customdid not rise above 10° C
2. stirringThe reaction mixture was stirred at 0° C. for 10 min
3. waitat room temperature for 60 h
4. extractionThe mixture was extracted with diethyl ether (2×100 ml)
5. washthe combined extracts were washed with brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo
8. customThe residue was purified by column chromatography (silica, 300 g)
9. washeluting with diethyl ether
10. concentrationconcentrated

ORD record

ord-66fda228a69046268c1aa61e2e5ed428

Source dataset

uspto-grants-2009_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07608604B2