Acetic Acid → 2-Amino-4-[(trifluoromethyl)thio]phenol

HRID 2094471Notes

Reaction equation

HRID 2094471 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([S:10][C:11]([F:14])([F:13])[F:12])[CH:7]=[CH:6][C:5]=1[OH:15])([O-])=O.C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:1][C:4]1[CH:9]=[C:8]([S:10][C:11]([F:14])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[OH:15]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 265966692-Nitro-4-((trifluoromethyl)thio)phenol

Product 1

HCID 230231052-Amino-4-[(trifluoromethyl)thio]phenolYield 41.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 5.49 g of 2-nitro-4-(trifluoromethylthio)phenol and 10 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 6.4 g of electrolytic iron, ml of acetic acid and 20 ml of water. The reaction mixture was stirred for 30 minutes. The mixture was cooled to room temperature, and then water was added, followed by extraction with ethyl acetate twice. 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. The residue was subjected to silica gel column chromatography to give 2.0 g of 2-amino-4-(trifluoromethylthio)phenol.

Workup

  1. additionwas added dropwise to a mixture, which
  2. extractionfollowed by extraction with ethyl acetate twice
  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-d658d7ea1ce540b6b52683cf173b3ebe
Source dataset
uspto-grants-2013_05
Patent number
US08445522B2

Reaction notes

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