Acetic Acid → 2-Amino-4-chloro-3-trifluoromethylphenol

HRID 1913723Notes

Reaction equation

HRID 1913723 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[C:3]=1[C:12]([F:15])([F:14])[F:13].C(OCC)(=O)C.C(O)(=O)C>[Fe].O>[NH2:9][C:4]1[C:3]([C:12]([F:13])([F:14])[F:15])=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 581482394-Chloro-2-nitro-3-(trifluoromethyl)phenol

Product 1

HCID 581482802-Amino-4-chloro-3-trifluoromethylphenolYield 80%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent2×

Procedure

A mixture of 1.57 g of 4-chloro-2-nitro-3-trifluoromethylphenol and 5 ml of ethyl acetate was added dropwise to a mixture, which was heated to 80° C., of 1.8 g of electrolytic iron, 7 ml of acetic acid and 7 ml of water, which was stirred 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 1.1 g of 2-amino-4-chloro-3-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-72b57d5ffad9439c84bbbb736a1c02b0
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

Loading…