Dimethylformamide → 2-Nitro-5-(3-nitrophenoxy)pyridine

HRID 1874320Notes

Reaction equation

HRID 1874320 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[N:16][CH:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[N+:18]([C:15]1[CH:14]=[CH:13][C:12]([O:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)=[CH:17][N:16]=1)([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 111373-NitrophenolHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 577491152-Nitro-5-(3-nitrophenoxy)pyridineYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3-nitrophenol (7.76 g, 55.8 mmol), 5-bromo-2-nitropyridine (10.3 g, 50.7 mmol), cesium carbonate (24.8 g, 76.1 mmol) and N,N-dimethylformamide (150 mL) was stirred at 50° C. for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=100/0→0/100) to give the title compound (4.37 g, 33%) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (NH silica gel, hexane/ethyl acetate=100/0→0/100)

Sources & evidence

ORD record
ord-61c3a775f1bc4aebb58828d59309736e
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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