Ammonium Chloride → 5-Bromo-2-ethylaniline

HRID 43326ノート

反応式

HRID 43326 の反応式
[Cl-].[NH4+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([N+:12]([O-])=O)[CH:5]=1>O.CO.[Zn]>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH3:11])=[C:6]([CH:5]=1)[NH2:12]

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 75669964-Bromo-1-ethyl-2-nitrobenzene

生成物 1

HCID 233467565-Bromo-2-ethylaniline収率 100%

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 887Methanol溶媒HCID 962Water溶媒2 回

実験手順

A solution of ammonium chloride (12.5 g, 0.2 mol) in water (30 ml) is added to a mixture of zinc dust (35.7 g, 0.5 mol) and 4-bromo-1-ethyl-2-nitrobenzene (18 g, 0.07 mol) in methanol (720 ml) and water (180 ml). The reaction mixture is refluxed for one hour, then cooled to room temperature and filtered through a plug of diatomaceous earth. The filtrate is concentrated in vacuo, then diluted with water and extracted with ethyl acetate. The combined organic extracts are washed with water and brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated in vacuo to yield 5-bromo-2-ethylaniline (14 g), used without further purification in the next step.

後処理

  1. temperatureThe reaction mixture is refluxed for one hour
  2. filtrationfiltered through a plug of diatomaceous earth
  3. concentrationThe filtrate is concentrated in vacuo
  4. additiondiluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts are washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate concentrated in vacuo

出典と根拠

ORDレコード
ord-3c6b334827a941978120e0e9895081d9
出典データセット
uspto-grants-2013_09
特許番号
US08536351B2

反応ノート

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