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/cyclohexane [1:10]
10. concentrationconcentrated

ORD record

ord-abaf67a19c5b43f0b8521994ca82ccb1

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622500B2