1-Bromo-3-iodo-5-nitrobenzene → 3-Bromo-5-iodoaniline

HRID 1941919Notes

Reaction equation

HRID 1941919 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[C:6]([I:8])[CH:7]=1>C(O)(=O)C.C(OCC)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([I:8])[CH:7]=1)[NH2:9]

Participants

5

Reactant 1

HCID 454803871-Bromo-3-iodo-5-nitrobenzene

Product 1

HCID 454803883-Bromo-5-iodoanilineYield 96.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-Bromo-5-iodonitrobenzene (4.21 g, 0.0128 mol) and iron powder (3.6 g, 0.0642 mol) in glacial acetic acid (50 ml) was stirred at ambient temperature for 16 h. The reaction mixture was then filtered through a pad of celite and washed through with ethyl acetate. The filtrate was evaporated in vacuo to give a brown oil. This was re-dissolved in ethyl acetate, loaded onto a large pad of silica and eluted with ethyl acetate. The filtrate was evaporated in vacuo to afford 3-Bromo-5-iodoaniline as a brown solid (3.67 g, 96%) which was used without further purification.

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. washwashed through with ethyl acetate
  3. customThe filtrate was evaporated in vacuo
  4. customto give a brown oil
  5. washeluted with ethyl acetate
  6. customThe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-92e8066e971945deb97ab11cc1d2fb2a
Source dataset
uspto-grants-2013_03
Patent number
US08389516B2

Reaction notes

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