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

HRID 1913716Notes

Reaction equation

HRID 1913716 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, 10 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-e1349a8ccdec4c42aeb17ac13badd779
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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