Phenol → 2-Nitro-5-phenoxypyridine

HRID 1454915Notes

Reaction equation

HRID 1454915 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[C:11]1[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[N:15][CH:16]=1.[Na+].[Cl-]>CN(C=O)C.[H][H]>[N+:17]([C:14]1[CH:13]=[CH:12][C:11]([O:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:16][N:15]=1)([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 996PhenolHCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 221794212-Nitro-5-phenoxypyridineYield 41.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

Phenol (306 mg) was dissolved in dry DMF (5 mL) and subsequently, sodium hydride (60% in mineral oil, 130 mg) was added which resulted in strong hydrogen gas evolution. The mixture was then allowed to stir at RT for 30 minutes. Subsequently, 5-bromo-2-nitro-pyridine (600 mg) was added und the resulting mixture was stirred at 60° C. for 12 hours. The reaction mixture was poured into ice water and the aqueous phase was saturated with NaCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane) to give 2-nitro-5-phenoxy-pyridine as a light yellow foam (267 mg). MS (EI): 216.1 (M+).

Workup

  1. stirringwas stirred at 60° C. for 12 hours
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, gradient of ethyl acetate in heptane)

Sources & evidence

ORD record
ord-c6e2819f068544c786664f2d64355a03
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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