(1,1'-Biphenyl)-2-ol → 1-(2-Fluoroethoxy)-2-phenylbenzene

HRID 1086010

Reaktionsgleichung

Reaktionsgleichung von HRID 1086010
[H-].[Na+].[C:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[OH:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CS(O[CH2:21][CH2:22][F:23])(=O)=O>CN(C)C=O>[F:23][CH2:22][CH2:21][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Komponenten

5

Edukt 3

HCID 7017(1,1'-Biphenyl)-2-olHCID 24758Sodium hydrideHCID 680342-Fluoroethyl methanesulfonate

Produkt 1

HCID 156713901-(2-Fluoroethoxy)-2-phenylbenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a suspension of sodium hydride (60 % oil dispersion; 4.0 g) in N,N-dimethylformamide (100 ml), 2-phenylphenol (17.0 g) was added at a temperature of 0 to 5° C., and the resultant mixture was stirred at room temperature for 1 hour. 2-Fluoroethyl methanesulfonate (14.2 g) was added thereto. The resulting mixture was heated to 90° C., followed by stirring for 5 minutes. The reaction mixture was poured onto ice-water and extracted with ethyl acetate. The extract was washed with aqueous potassium carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent, toluene) to give 1-(2-fluoroethoxy)-2-phenylbenzene (Compound No. 20) (16.4 g). nD24.8 1.5796.

Aufarbeitung

  1. additionwas added at a temperature of 0 to 5° C.
  2. additionThe reaction mixture was poured onto ice-water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with aqueous potassium carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent, toluene)

Quellen und Nachweise

ORD-Eintrag
ord-00740c94dc8a4bf7910ad7562c902468
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05012004

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