Trifluoroacetic acid → 3,5-Dichloro-4-ethoxyaniline

HRID 2230846Notes

Reaction equation

HRID 2230846 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:20]=[C:19]([Cl:21])[C:18]([O:22][CH2:23][CH3:24])=[C:17]([Cl:25])[CH:16]=1)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:21][C:19]1[CH:20]=[C:15]([NH2:14])[CH:16]=[C:17]([Cl:25])[C:18]=1[O:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 54404293(3,5-Dichloro-4-ethoxy-phenyl)-carbamic acid tert-butyl ester

Product 1

HCID 152708843,5-Dichloro-4-ethoxyaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trifluoroacetic acid (5 mL) is added to solid (3,5-dichloro-4-ethoxy-phenyl)-carbamic acid tert-butyl ester (0.97 g) and the mixture is stirred for approximately 45 minutes at room temperature. Water is then added, and the mixture is cooled in an ice bath and basified with solid potassium carbonate. The solution is extracted three times with ethyl acetate and the combined organic phases are washed with saturated aqueous sodium chloride then dried over anhydrous sodium sulfate. Concentration under reduced pressure and recrystallization from hexanes provides the desired product as a pale yellow crystalline solid.

Workup

  1. temperaturethe mixture is cooled in an ice bath
  2. extractionThe solution is extracted three times with ethyl acetate
  3. washthe combined organic phases are washed with saturated aqueous sodium chloride
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. concentrationConcentration
  6. customunder reduced pressure and recrystallization from hexanes

Sources & evidence

ORD record
ord-218b1f2188674b9d97fd1a89151a55f1
Source dataset
uspto-grants-2002_07
Patent number
US06426355B1

Reaction notes

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