4-Nitrophenol → 4-Chloro-6-(4-nitrophenoxy)pyrimidine

HRID 853219Notes

Reaction equation

HRID 853219 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([O-:11])=[O:10].[H-].[Na+]>[Cl-].[Na+].O>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([O:18][C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[CH:7]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 24758Sodium hydrideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 143638504-Chloro-6-(4-nitrophenoxy)pyrimidineYield 55.3%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

After adding 4,6-dichloropyrimidine (750 mg) to a suspension of 4-nitrophenol (700 mg) and sodium hydride (60%) (200 mg) indimethylformamide (13 ml) at 0° C., the mixture was heated and stirred at 80° C. for 1.5 hours. The reaction solution was poured into saturated brine and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and then concentrated. The obtained residue was passed through an NH silica gel column (Fuji Silysia Chemical), eluted with a solvent (ethyl acetate-hexane=1–4) and concentrated to obtain 700 mg of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated
  5. washeluted with a solvent (ethyl acetate-hexane=1–4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9b74e88f82ed460293482912fca987b4
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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