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

HRID 2405452Notes

Reaction equation

HRID 2405452 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 26.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

10 g (49.5 mmol) of 2-bromonitrobenzene, 13 g (163 mmol) of sodium acetate, and 10 g (59 mmol) of 4-bromoaniline were stirred at 180° C. for 8 hours in an argon atmosphere. After cooling the reaction solution to room temperature, the reaction solution was diluted with ethyl acetate, and filtered. After concentrating the filtrate, the residue was washed with methanol to obtain 3.8 g of (4-bromophenyl)-(2-nitrophenyl)amine as an orange crystal (yield: 22%).

Workup

  1. filtrationfiltered
  2. concentrationAfter concentrating the filtrate
  3. washthe residue was washed with methanol

Sources & evidence

ORD record
ord-087beb95ae97492fbda61fd321ad42c7
Source dataset
uspto-grants-2014_08
Patent number
US08803420B2

Reaction notes

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