Acetic Acid → 2-Amino-5-chloro-4-(trifluoromethyl)phenol

HRID 884963Notes

Reaction equation

HRID 884963 reaction equation
[Cl:1][C:2]1[C:3]([C:12]([F:15])([F:14])[F:13])=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1.C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:9][C:5]1[CH:4]=[C:3]([C:12]([F:13])([F:14])[F:15])[C:2]([Cl:1])=[CH:7][C:6]=1[OH:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 107765045-Chloro-2-nitro-4-(trifluoromethyl)phenol

Product 1

HCID 140117362-Amino-5-chloro-4-(trifluoromethyl)phenolYield 81.7%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 7.55 g of 5-chloro-2-nitro-4-trifluoromethylphenol and 10 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 8.7 g of electrolytic iron, 30 ml of acetic acid and 50 ml of water, and then the reaction mixture was stirred at the same temperature for 30 minutes. The mixture was cooled to room temperature, and then water was added, followed by extraction 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. The residue was subjected to silica gel column chromatography to give 5.4 g of 2-amino-5-chloro-4-trifluoromethylphenol.

Workup

  1. additionwas added dropwise to a mixture, which
  2. extractionfollowed by extraction 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-b0a00884c8864bc6aeb8206ce50eb34b
Source dataset
uspto-grants-2012_08
Patent number
US08242133B2

Reaction notes

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