1-bromo-3-ethyl-5-nitroBenzene → 3-Bromo-5-ethylaniline

HRID 1452051Notes

Reaction equation

HRID 1452051 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:10]([O-])=O)[CH:5]=[C:6]([CH2:8][CH3:9])[CH:7]=1>C(O)(=O)C.C(O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([CH2:8][CH3:9])[CH:7]=1)[NH2:10]

Participants

5

Reactant 1

HCID 189298701-bromo-3-ethyl-5-nitroBenzene

Product 1

HCID 189298993-Bromo-5-ethylaniline

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

Dissolve 3-bromo-5-ethylnitrobenzene (6.21g, 27mmol) in acetic acid (40mL) and ethanol (30mL) and treat with iron powder (2.7g). Reflux for 3 hours, filter through Celite and evaporate the solvent in vacuo. Purify by silica gel chromatography to give 3-bromo-5-ethylaniline.

Workup

  1. temperatureReflux for 3 hours
  2. filtrationfilter through Celite
  3. customevaporate the solvent in vacuo
  4. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-b46620aeb06f4cf682d50726ac488bb8
Source dataset
uspto-grants-1997_02
Patent number
US05606063

Reaction notes

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