Aniline → 5-bromo-2-nitro-n-phenylaniline

HRID 1051462Notes

Reaction equation

HRID 1051462 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20](F)[CH:19]=1>CS(C)=O.O>[Br:17][C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[C:20]([CH:19]=1)[NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 81531DiisopropylethylamineHCID 27833624-Bromo-2-fluoro-1-nitrobenzene

Product 1

HCID 2386965-bromo-2-nitro-n-phenylaniline

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Aniline (930 mg, 10.0 mmol) was added to a solution of DIPEA (1.94 g, 15.0 mmol) and 4-bromo-2-fluoro-1-nitrobenzene (2.2 g, 10.0 mmol) in DMSO (16 mL). The reaction mixture was stirred at 60° C. for 4 h. Upon completion, the mixture was diluted with water (50 mL), and the resulting precipitate collected by filtration, washed with water and dried in vacuo. The crude product was used in next step without further purification. LCMS (m/z): 293.1/294.1 [M+H]+/[M+2H]+

Workup

  1. filtrationthe resulting precipitate collected by filtration
  2. washwashed with water
  3. customdried in vacuo
  4. customThe crude product was used in next step without further purification

Sources & evidence

ORD record
ord-3dbff394126847cc9c49e4b3ab7e6a30
Source dataset
uspto-grants-2016_07
Patent number
US09388173B2

Reaction notes

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