Water → 4-Bromo-2,6-dinitroaniline

HRID 44462

Reaction equation

HRID 44462 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 96.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A stirred suspension of 2,6-dinitroaniline (5 g, 27.3 mmol) in glacial acetic acid (50 mL) was added bromine (1.5 mL, 30 mmol) dropwise and heated at 120° C. for 2 h. After cooling to ambient temperature, the resultant mixture was poured into water (50 mL). The precipitate solid was collected by filtration and washed with water then dried in-vacuo. The solid was re-dissolved in EtOAC, washed with water and saturated brine. The organic layer was collected and concentrated in-vacuo to give the desired product (6.88 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ ppm 8.37 (br s, 2H), 8.58 (s, 2H).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationThe precipitate solid was collected by filtration
  3. washwashed with water
  4. customthen dried in-vacuo
  5. dissolutionThe solid was re-dissolved in EtOAC
  6. washwashed with water and saturated brine
  7. customThe organic layer was collected
  8. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-5dd376713d8e49fe9c13b12141dbd963
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Linked notes

Loading…