Sulfuric Acid → 3-(Pentafluorothio)phenol

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence