Sulfuric Acid → 3-(Pentafluorothio)phenol

HRID 269415Notes

Reaction equation

[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)N.[OH:14]S(O)(=O)=O.N([O-])=O.[Na+]>O>[F:1][S:2]([F:13])([F:12])([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:14])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5.0 g of 3-pentafluorosulfanylaniline were suspended in 50 ml of a 35% aqueous H2SO4 solution. Then, at 0° C., a solution of 1.57 g of NaNO2 in 5 ml of water was added dropwise over the course of 10 minutes. The mixture was stirred at 0° C. for 40 minutes. Then a solution, cooled to 0° C., of 8.56 g of Cu(NO3)2 in 50 ml of water was added to this suspension. Immediately thereafter, 3.26 g of Cu2O was also added, whereupon marked evolution of gas was observable. 3 extractions each with 100 ml of CH2Cl2 were carried out, the org. phase washed with 100 ml of a saturated aqueous NaCl solution and dried over MgSO4, and the solvent was removed in vacuo. Chromatography with DIP on a short silica gel column afforded 3.5 g of the phenol as colorless oil.

Workup

additionwas added to this suspension
extraction3 extractions each with 100 ml of CH2Cl2
washphase washed with 100 ml of a saturated aqueous NaCl solution
dry with materialdried over MgSO4
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-877e882a705e43f1a9ec78245555e0fe
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446225B2

Reaction notes

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