2-Bromo-1-fluoro-3,5-dinitrobenzene → 2-Bromo-3-fluoro-5-nitroaniline

HRID 710207Notes

Reaction equation

HRID 710207 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-])=O>CC(O)=O.CCOC(C)=O.C([O-])(O)=O.[Na+].[Fe]>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[NH2:12]

Participants

6

Reactant 1

HCID 580657782-Bromo-1-fluoro-3,5-dinitrobenzene

Product 1

HCID 580658062-Bromo-3-fluoro-5-nitroanilineYield 52.6%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 2-bromo-1,5-dinitro-3-fluorobenzene (100 mg, 0.38 mmol, 1 equiv) and iron powder (64 mg, 1.14 mmol, 3 equiv) in 3 mL of HOAc was stirred at room temperature for 90 minutes. The reaction mixture was diluted with EtOAc (20 mL) and saturated NaHCO3 (to ca. pH 7-8). The organic layer was separated and evaporated under vacuum. The crude residue was purified by column chromatography on silica gel using EtOAc/hexanes (1:4) as eluent to give 47 mg of 2-bromo-3-fluoro-5-nitroaniline (52%).

Workup

  1. customThe organic layer was separated
  2. customevaporated under vacuum
  3. customThe crude residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e6604faab81d4da1995cfefa6b26dff4
Source dataset
uspto-grants-2015_11
Patent number
US09181222B2

Reaction notes

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