Water → 4-Bromo-2,6-dinitroaniline

HRID 447018

Reaction equation

HRID 447018 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[C:5]=1[NH2:6])([O-:3])=[O:2].[Br:14]Br.O>C(O)(=O)C>[Br:14][C:9]1[CH:10]=[C:4]([N+:1]([O-:3])=[O:2])[C:5]([NH2:6])=[C:7]([N+:11]([O-:13])=[O:12])[CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 690702,6-Dinitroaniline

Product 1

HCID 37466084-Bromo-2,6-dinitroanilineYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred suspension of 2,6-dinitroaniline (5 g, 27.3 mmol) in glacial acetic acid (50 ml) was treated, dropwise, with bromine (1.5 ml, 30 mmol) and heated at 120° C. for 2 h. After cooling to ambient temperature, the resultant mixture was poured into water (500 ml). The precipitated solid was collected by filtration, washed with water and dried in vacuo to give 4-Bromo-2,6-dinitroaniline as a yellow solid (6.5 g, 91%).

Workup

  1. additionwas treated
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9fa5d37bf03f424d843ef24b0bbe5d8b
Source dataset
uspto-grants-2013_07
Patent number
US08481544B2

Linked notes

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