Aniline → (2-Bromo-6-nitrophenyl)phenylamine

HRID 243147Notes

Reaction equation

HRID 243147 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1F.[NH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 404274461-Bromo-2-fluoro-3-nitrobenzene

Product 1

HCID 68157569(2-Bromo-6-nitrophenyl)phenylamine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-bromo-2-fluoro-3-nitrobenzene (5 g, 22.7 mmol) and aniline (4.2 mL, 45 mmol) in DMSO (10 mL, 2M) in a sealed flask was evacuated and purged with argon. The mixture was heated at 100° C. for 12 h. The cooled mixture was diluted with KHSO4 (aq. satd. solution, 100 mL) and brine, dried (Na2SO4) and concentrated to give the product (2-bromo-6-nitrophenyl)phenylamine as a bright orange solid (6.5 g, quant.). 1H NMR (400 MHz, CDCl3): δ 7.96 (1H, dd, J=8.5, 1.7 Hz), 7.86 (1H, br s), 7.75 (1H, dd, J=8.2, 1.5 Hz), 7.16-7.22 (2H, m), 6.90-6.99 (2H, m), 6.77 (2H, m).

Workup

  1. custompurged with argon
  2. additionThe cooled mixture was diluted with KHSO4 (aq. satd. solution, 100 mL) and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fd6eb44b93e34687b3f36eb157b83931
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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