4-Chlorophenol → Pyrimidine, 4-chloro-6-(4-chlorophenoxy)-

HRID 1855398Notes

Reaction equation

HRID 1855398 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>C(#N)C.[I-].[Na+]>[Cl:8][C:6]1[CH:7]=[C:2]([O:16][C:13]2[CH:14]=[CH:15][C:10]([Cl:9])=[CH:11][CH:12]=2)[N:3]=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 46844-ChlorophenolHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 3079025Pyrimidine, 4-chloro-6-(4-chlorophenoxy)-Yield 93%

Reagents, catalysts & solvents 2

HCID 5238Sodium IodideCatalystHCID 6342AcetonitrileSolvent

Procedure

4,6-Dichloropyrimidine (149 mg, 1 mmol), 4-chlorophenol (135 mg, 1.05 mmol), potassium carbonate (166 mg, 1.2 mmol) and sodium iodide (7.5 mg, 0.05 mmol) were stirred in acetonitrile (3 mL) at 20° C. under an atmosphere of nitrogen for 16 h. The reaction was poured onto 1 N aqueous sodium hydroxide solution and the mixture was extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The title compound (224 mg, 93%) was obtained as a pale-yellow solid.

Workup

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9604e9bc6533485688207cf92a1f9182
Source dataset
uspto-grants-2015_02
Patent number
US08962834B2

Reaction notes

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