Water → 5-Bromo-2-phenoxypyrimidine

HRID 432175

Reaktionsgleichung

Reaktionsgleichung von HRID 432175
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C:9]1([OH:15])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[K+].O>C1(C)C=CC=CC=1.C1OCCOC2C(=CC=CC=2)OCCOCCOC2C(=CC=CC=2)OC1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:15][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 996PhenolHCID 14797Potassium HydroxideHCID 6066655-Bromo-2-chloropyrimidine

Produkt 1

HCID 6428425-Bromo-2-phenoxypyrimidineAusbeute 54,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 26541Dibenzo-18-crown-6KatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 5-bromo-2-chloropyrimidine (5.00 g, 0.0259 mol), phenol (3.16 g, 0.0336 mol), dibenzo-18-crown-6 (0.47 g, 0.0013 mol) and ground potassium hydroxide (3.51 g, 0.0626 mol) in toluene (75 ml) was heated at reflux for 5 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. The residue was purified by flash column chromatography on silica using n-heptane/ethyl acetate (98:2) as an eluent to give 5-bromo-2-phenoxy-pyrimidine as a white solid (3.55 g, 0.0141 mol): 1H NMR (DMSO-d6, 400 MHz) 8.80 (s, 2H), 7.45 (t, 2H), 7.27 (t, 1H), 7.22 (d 2H); TLC (n-heptane/ethyl acetate=95:5) Rf 0.20.

Aufarbeitung

  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
  9. customThe residue was purified by flash column chromatography on silica

Quellen und Nachweise

ORD-Eintrag
ord-1bbc8bd3d0a34185a80347e464788c0c
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660744B1

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