Sodium hydride → 2-(2,4-Difluorophenoxy)-5-methyl-4-nitropyridine-1-oxide

HRID 230139Notes

Reaction equation

HRID 230139 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[OH:11].Cl[C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([CH3:22])=[CH:15][N+:14]=1[O-:23]>C1COCC1>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[O:11][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[C:16]([CH3:22])=[CH:15][N+:14]=1[O-:23]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1230512,4-DifluorophenolHCID 123180102-Chloro-5-methyl-4-nitropyridine N-oxide

Product 1

HCID 598342802-(2,4-Difluorophenoxy)-5-methyl-4-nitropyridine-1-oxideYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium hydride (0.47 g, 60% in oil) in 50 mL of THF was added dropwise a solution of 1 mL of 2,4-difluorophenol in 10 mL of THF. The reaction mixture was stirred for one hour, and 2-chloro-5-methyl-4-nitropyridine-1-oxide (2.0 g) was added slowly. The resulting mixture was stirred at reflux for 8 hours and at room temperature overnight. The solvent was removed and the light yellow solid isolated by extraction with methylene chloride. Purification via chromatography (silica gel, ethyl acetate/hexane, 1:1) gave 1.65 g of 2-(2,4-difluorophenoxy)-5-methyl-4-nitropyridine-1-oxide (55% yield). Mass Spec. M+H=283.

Workup

  1. stirringThe resulting mixture was stirred
  2. customThe solvent was removed
  3. customthe light yellow solid isolated by extraction with methylene chloride
  4. customPurification via chromatography (silica gel, ethyl acetate/hexane, 1:1)

Sources & evidence

ORD record
ord-90446cd55b61424dbd309243c4233efa
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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