1,3-dibromo-5-nitrobenzene → 3,5-Dibromoaniline

HRID 1354840Notes

Reaction equation

HRID 1354840 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-])=O)[CH:5]=[C:6]([Br:8])[CH:7]=1>CC(O)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([Br:8])[CH:7]=1)[NH2:9]

Participants

3

Reactant 1

HCID 2387111,3-dibromo-5-nitrobenzene

Product 1

HCID 2215123,5-DibromoanilineYield 85.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a scale up reaction using the same procedure as described above, 5 g (17.9 mmol) of 3,5-dibromonitrobenzene (262), 30 mL of TiCl3 (30% wt. in 2.0 N aqueous HCl) and AcOH (125 mL) were used. After 4 h reaction and subsequent work-up, 3.85 g (85.7% yield) of 3,5-dibromoaniline (273) was obtained.

Workup

  1. customIn a scale up reaction
  2. customAfter 4 h reaction and subsequent work-up

Sources & evidence

ORD record
ord-fc1d7fc559f44c58b1b78acb386c8451
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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