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

HRID 1913720

Reaction equation

HRID 1913720 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([OH:12])=[C:4]([N+:13]([O-])=O)[CH:3]=1.C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]([C:8]([F:11])([F:9])[F:10])=[CH:6][C:5]=1[OH:12]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 668796884-Chloro-2-nitro-5-(trifluoromethyl)phenol

Product 1

HCID 668804782-Amino-4-chloro-5-(trifluoromethyl)phenolYield 84.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 2.3 g of 4-chloro-2-nitro 5-trifluoromethylphenol and 10 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 2.6 g of electrolytic iron, 10 ml of acetic acid and 20 ml of water, and then the reaction mixture was stirred for one hour. 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 1.7 g of 2-amino-4-chloro-5-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-ce85c188db534853a7ebc1de2f3aea15
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Linked notes

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