Ammonium Chloride → 5-Bromo-2-ethylaniline

HRID 1027379Notes

Reaction equation

HRID 1027379 reaction equation
[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]

Participants

6

Reactant 2

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

Product 1

HCID 233467565-Bromo-2-ethylanilineYield 100%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f8f6e88596424ef6b9dbfb22bcd418cb
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Reaction notes

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