Cesium carbonate → 4-(2-Methyl-4-nitrophenoxy)-2-nitrobenzenamine

HRID 240556Notes

Reaction equation

HRID 240556 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH3:11].[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=1[N+:20]([O-:22])=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH3:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[O:19][C:16]1[CH:17]=[CH:18][C:13]([NH2:12])=[C:14]([N+:20]([O-:22])=[O:21])[CH:15]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 37588824-Amino-3-Nitrophenol

Product 1

HCID 866508954-(2-Methyl-4-nitrophenoxy)-2-nitrobenzenamineYield 87.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-fluoro-2-methyl-4-nitrobenzene (2.02 g, 13.0 mmol) and 4-amino-3-nitrophenol (2.22 g, 14.4 mmol) in DMF (20 mL) was added cesium carbonate (5.28 g, 16.2 mmol). After heating to 60° C. for 10 hours, the mixture was diluted with water (100 mL) and filtered. The precipitate was washed with water and air-dried to provide the product (3.28 g, 87%) as dark solid.

Workup

  1. filtrationfiltered
  2. washThe precipitate was washed with water
  3. customair-dried

Sources & evidence

ORD record
ord-e9d0a5f760c24f62b24b9838c724eeb4
Source dataset
uspto-grants-2014_02
Patent number
US08648087B2

Reaction notes

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