Sulfuric Acid → 3-(Pentafluorothio)phenol

Temperature

0 °C

5.0 g of 3-pentafluorosulfanylaniline (Tetrahedron 56, (2000) 3399) were suspended in 50 ml of a 35% aqueous H2SO4 solution. At 0° C., a solution of 1.57 g of NaNO2 in 5 ml of water was then added dropwise within 10 minutes. The mixture was stirred at 0° C. for a further 40 minutes. A solution, cooled to 0° C., of 8.56 g of Cu(NO3)2 in 50 ml of water was then added to this suspension. Directly thereafter, 3.26 g of Cu2O were also added, and distinct gas evolution could be observed. The mixture was extracted 3 times with 100 ml each time of CH2Cl2, the organic phase was washed with 100 ml of a saturated aqueous NaCl solution and dried over MgSO4, and the solvent was removed under reduced pressure. Chromatography on silica gel with DIP afforded 3.5 g of the phenol as a colorless oil.

1. additionwas then added to this suspension
2. extractionThe mixture was extracted 3 times with 100 ml each time of CH2Cl2
3. washthe organic phase was washed with 100 ml of a saturated aqueous NaCl solution
4. dry with materialdried over MgSO4
5. customthe solvent was removed under reduced pressure

ORD record

ord-0a18eaccb1194a26bdaf325e2d00fcd0

Source dataset

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07763661B2