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

HRID 1750791노트

반응식

HRID 1750791 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-98801440c4a840a58f592124dd379132
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156860B2

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