1-Bromo-3-chloro-5-nitrobenzene → 3-Bromo-5-chloroaniline

HRID 1628285Notes

Reaction equation

HRID 1628285 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[C:4]([Cl:11])[CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([Cl:11])[CH:3]=1

Participants

4

Reactant 1

HCID 178398381-Bromo-3-chloro-5-nitrobenzene

Product 1

HCID 30847093-Bromo-5-chloroanilineYield 99.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

1-bromo-3-chloro-5-nitrobenzene (4.27 g, 18.0 mmol) was dissolved in acetic acid (24.1 mL μl, 18.0 mmol) then zinc dust (11.82 g, 180 mmol) was added. After 4 h the reaction was filtered and concentrated to afford 3-bromo-5-chlorobenzenamine (3.7 g, 99% yield).

Workup

  1. filtrationAfter 4 h the reaction was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-12fc8808669d4aca9dc5798bbb8edda5
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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