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

HRID 2190840Notes

Reaction equation

HRID 2190840 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-0683dc008f754bdc8803e10f7026cd89
Source dataset
uspto-grants-2012_12
Patent number
US08324387B2

Reaction notes

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