Nitric Acid → 2-Nitro-4-((trifluoromethyl)thio)phenol

Reaction equation

[F:1][C:2]([F:12])([F:11])[S:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[N+:13]([O-])([OH:15])=[O:14].S(=O)(=O)(O)O>C(O)(=O)C>[N+:13]([C:6]1[CH:5]=[C:4]([S:3][C:2]([F:11])([F:1])[F:12])[CH:9]=[CH:8][C:7]=1[OH:10])([O-:15])=[O:14]

Participants

Procedure

To a mixture of 4.8 g of 4-(trifluoromethylthio)phenol and 20 ml of acetic acid, a mixture of 2.5 g of 70% nitric acid and 1 ml of acetic acid and then 1.5 ml of concentrated sulfuric acid were added dropwise with the internal temperature kept at 10-15° C. The reaction mixture was stirred for three hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed with water, a saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate, and then concentrated under reduced pressure to give 5.94 g of 2-nitro-4-(trifluoromethylthio)phenol.