4-Iodophenol → 2-(4-Iodophenoxy)pyrimidine

HRID 1752044Notes

Reaction equation

HRID 1752044 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1>CN(C=O)C.[Cl-].[Na+].O>[I:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 744042-Chloropyrimidine

Product 1

HCID 14846172-(4-Iodophenoxy)pyrimidineYield 97.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

Under an argon atmosphere, potassium carbonate (207 mg) was added to a solution of 4-iodophenol (220 mg) and 2-chloropyrimidine (114 mg) in DMF (1 ml), and the resulting mixture was stirred at 120° C. for 3 hours. The reaction solution was cooled to room temperature and saturated brine was added thereto, followed by extracting the resulting mixture with chloroform. Organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=3/1) to obtain 2-(4-iodophenoxy)pyrimidine (288 mg). NMR (1′, CDCl3): δ 6.97-7.00 (2H, m), 7.06 (1H, t, J=4.6 Hz), 7.73-7.75 (2H, m), 8.57 (2H, d, J=4.6 Hz)

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionby extracting the resulting mixture with chloroform
  3. washOrganic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter removing anhydrous sodium sulfate
  6. filtrationby filtration
  7. concentrationthe filtrate was concentrated
  8. customThe residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-a12596d4f3fe456782d238d9a882f497
Source dataset
uspto-grants-2015_10
Patent number
US09162988B2

Reaction notes

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