Sulfuric Acid → 4-Hydroxyphenylsulfur pentafluoride

Participants

Reaction Conditions

Reaction Steps

40.00 g of 4-pentafluorosulfanylaniline (Tetrahedron 56, (2000) 3399) were suspended in 500 ml of a 35% aqueous H2SO4 solution. At 0° C., a solution of 13.85 g of NaNO2 in 30 ml of water was then added dropwise within 10 minutes. The mixture was stirred at 0° C. for a further 35 minutes. A solution, cooled to 0° C., of 171.10 g of Cu(NO3)2 in 200 ml of water was then added to this suspension. Directly thereafter, 26.11 g of Cu2O were also added, and distinct gas evolution could be observed. The mixture was stirred at RT for a further 2 hours, then the mixture was extracted 3 times with 200 ml each time of CH2Cl2, the combined organic phases were 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