Water → 4-Methyl-5-nitro-2-phenoxy-pyridine

HRID 491866Notes

Reaction equation

HRID 491866 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](=O)([O-])[O-].[Cs+].[Cs+].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.O>CN(C=O)C>[CH3:8][C:19]1[C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=[C:15]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 996PhenolHCID 10796Cesium carbonateHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 576783574-Methyl-5-nitro-2-phenoxy-pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of phenol (0.30 g, 3.1 mmol) in DMF (10 mL) was treated with cesium carbonate (1.41 g, 4.3 mmol) and stirred for 15 min. 2-Chloro-5-nitro pyridine (0.5 g, 2.9 mmol) was added, and the reaction mixture was stirred and monitored via TLC. After the reaction was complete, the reaction mixture was treated with water, extracted into EtOAc, and the organic extract washed with 1N NaOH and brine, dried (Na2SO4) and concentrated to yield 4-methyl-5-nitro-2-phenoxypyridine as a solid.

Workup

  1. stirringthe reaction mixture was stirred
  2. extractionextracted into EtOAc
  3. extractionthe organic extract
  4. washwashed with 1N NaOH and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-34d218adfcdb459eb1e533bfe9bf77b1
Source dataset
uspto-grants-2009_05
Patent number
US07531545B2

Reaction notes

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