Cesium carbonate → 3-(2-Chloro-4-phenoxyphenoxy)-propanol

HRID 479643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 479643
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:15].Br[CH2:17][CH2:18][CH2:19][OH:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:4][C:3]=1[O:15][CH2:17][CH2:18][CH2:19][OH:20]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 123083-Bromo-1-propanolHCID 107276802-chloro-4-phenoxyPhenol

Produkt 1

HCID 187722773-(2-Chloro-4-phenoxyphenoxy)-propanolAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 100 ml DMF solution of 2-chloro-4-phenoxyphenol (10 g, 45 mmol) were added 3-bromopropanol (8.2 ml, 91 mmol) and cesium carbonate (6.2 g, 50 mmol). The resulting suspension was heated to 70° C. for 7 hr. Solvent was removed under reduced pressure. The residue was diluted with AcOEt and water. The organic layer was separated. The aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 30% AcOEt/hexanes gave 3-(2-chloro-4-phenoxyphenoxy)-propanol 11.96 g (95%). This material was dissolved in acetonitrile 200 ml. To it was added triphenylphosphine (18.5 g, 55.8 mmol) and carbon tetrabromide (16.9 g, 64.4 mmol). After stirring at rt for 1 hr, the solvent was removed, and the residue was chromatographed on silica gel. Elution with 5% THF/hexanes gave the title compound as colorless oil 10.9 g (74%).

Aufarbeitung

  1. customSolvent was removed under reduced pressure
  2. additionThe residue was diluted with AcOEt and water
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted twice with AcOEt
  5. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customchromatographed on silica gel
  9. washElution with 30% AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c3069c81e74b489382b904c9e630e86c
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06645997B2

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