Ethyl Acetate → 3,5-Dichloro-4-(2,2,2-trifluoroethoxy)aniline

HRID 532171Notes

Reaction equation

HRID 532171 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][CH2:13][C:14]([F:17])([F:16])[F:15].Cl[Sn]Cl.[OH-].[Na+].CC(=O)OCC>CO.Cl>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:11])[C:3]=1[O:12][CH2:13][C:14]([F:15])([F:16])[F:17])[NH2:8]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 138522271,3-Dichloro-5-nitro-2-(2,2,2-trifluoroethoxy)benzene

Product 1

HCID 138521463,5-Dichloro-4-(2,2,2-trifluoroethoxy)anilineYield 94%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

To a solution of 1,3-dichloro-5-nitro-2-(2,2,2-trifluoroethoxy)benzene (1.90 g, 6.55 mmol) in MeOH (20 mL) and 12 N HCl (20 mL) at rt, SnCl2 (3.72 g, 19.66 mmol) was slowly added to it and then the reaction mixture was stirred overnight at rt. To the reaction mixture was slowly added 3N NaOH to pH=10 and then extracted with EA. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel eluted with PE:EA (6:1) to provide 3,5-dichloro-4-(2,2,2-trifluoroethoxy)aniline (1.60 g, yield 94%) as pale yellow oil.

Workup

  1. extractionextracted with EA
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography over silica gel
  6. washeluted with PE

Sources & evidence

ORD record
ord-ae1e0c4f0cb74bbb84f8d051cd35e0bd
Source dataset
uspto-grants-2014_10
Patent number
US08853186B2

Reaction notes

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