Phenol → 2-Phenoxypyrimidine

HRID 432180Notes

Reaction equation

HRID 432180 reaction equation
Cl[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]1([OH:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1.[OH-].[K+]>C1(C)C=CC=CC=1.O>[O:14]([C:5]1[N:4]=[CH:3][CH:2]=[CH:7][N:6]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 14797Potassium HydroxideHCID 26541Dibenzo-18-crown-6HCID 126003845-Chloropyrimidine

Product 1

HCID 53247682-Phenoxypyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 5-chloropyrimidine (5.00 g, 0.0437 mol), phenol (5.38 g, 57.2 mmol), dibenzo-18-crown-6 (0.84 g, 0.0023 mol) and ground potassium hydroxide (5.92 g, 0.1055 mol) in toluene (75 ml) was heated at reflux for 3 hours with azeotropic removal of water. The mixture was allowed to cool to ambient temperature and the solvent was removed under reduced pressure. The residue was partitioned between water and chloroform. The layers were separated and the aqueous phase was extracted with chloroform three times. The combined organic layers were dried over magnesium sulfate, filtered and evaporated to give 2-phenoxypyrimidine as a white powder (95% pure, 4.56 g, 0.0265 mol): 1H NMR (CDCl3, 400 MHz) 8.57 (d, 2H), 7.43 (t, 2H), 7.26 (t, 1H), 7.20 (d 2H); TLC (n-heptane/ethyl acetate=1:1) Rf 0.42.

Workup

  1. temperaturewas heated
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was partitioned between water and chloroform
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with chloroform three times
  6. dry with materialThe combined organic layers were dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-f4478a10157b48f79244caf147f3162b
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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