4-Bromoaniline → N-(4-bromophenyl)-2-nitroaniline

HRID 420459Notes

Reaction equation

HRID 420459 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C([O-])(=O)C.[Na+].[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1>C(OCC)(=O)C>[Br:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 113411-Bromo-2-nitrobenzeneHCID 517045Sodium Acetate

Product 1

HCID 12000290N-(4-bromophenyl)-2-nitroanilineYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

A mixture made from 10 g (49.5 mmol) of 2-bromo nitrobenzene, 13 g (163 mmol) of sodium acetate and 10 g (59 mmol) of 4-bromo aniline was stirred with heating at the temperature of 180° C. under the atmosphere of nitrogen gas for 8 hours. The reacted solution was cooled down to room temperature, diluted with ethyl acetate and filtered. After concentrating the filtrate, and by washing the residue with methanol 3.8 g of (4-bromophenyl)-(2-nitrophenyl) amine was obtained as orange crystals (yield: 22%).

Workup

  1. temperatureThe reacted solution was cooled down to room temperature
  2. filtrationfiltered
  3. concentrationAfter concentrating the filtrate
  4. washby washing the residue with methanol 3.8 g of (4-bromophenyl)-(2-nitrophenyl) amine

Sources & evidence

ORD record
ord-4dc8c0d309a64b7eb18b65d9c873b6da
Source dataset
uspto-grants-2012_01
Patent number
US08097349B2

Reaction notes

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