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

HRID 884952Notes

Reaction equation

HRID 884952 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

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 38151584-(Trifluoromethylsulfanyl)phenol

Product 1

HCID 265966692-Nitro-4-((trifluoromethyl)thio)phenolYield 100.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

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.

Workup

  1. customkept at 10-15° C
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and a saturated sodium chloride solution, dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-efc2a1e46e2e4812bbd5f9a602b1cbc3
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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