2,4-Dinitroaniline → 2-Bromo-4,6-dinitroaniline

HRID 429577

Reaction equation

HRID 429577 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[Br:14]Br>CC(O)=O.CCOC(C)=O>[N+:1]([C:4]1[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[C:7]([Br:14])[C:5]=1[NH2:6])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 73212,4-DinitroanilineHCID 24408Bromine

Product 1

HCID 157522-Bromo-4,6-dinitroanilineYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,4-dinitroaniline (2.2 g, 12 mmol) in 40 ml of AcOH was added 1.0 ml of Br2 dropwise and reaction mixture was stirred for 1 h. The reaction mixture was concentrated in vacua, yielding a dark residue which was diluted with EtOAc and washed with aqueous NaHCO3. Organic layer was dried over MgSO4 and concentrated in vacuo to provide 2.9 g (11 mmol, 92%) of 2,4-dinitro-6-bromo-aniline which was characterized by NMR and used in a following reaction without further purification.

Workup

  1. customreaction mixture
  2. concentrationThe reaction mixture was concentrated in vacua
  3. customyielding a dark residue which
  4. washwashed with aqueous NaHCO3
  5. dry with materialOrganic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bde4e98607de4456a69db25611a525f3
Source dataset
uspto-grants-2001_11
Patent number
US06316637B1

Linked notes

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