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

HRID 1750791

反応式

HRID 1750791 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-98801440c4a840a58f592124dd379132
出典データセット
uspto-grants-2015_10
特許番号
US09156860B2

関連ノート

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