Diphosgene → 5-Fluoro-2(3H)-benzoxazolone

HRID 1533881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1533881
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].Cl[C:11](OC(Cl)(Cl)Cl)=[O:12]>O1CCCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[O:9][C:11](=[O:12])[NH:1][C:2]=2[CH:7]=1

Komponenten

4

Edukt 2

HCID 10426DiphosgeneHCID 27359172-Amino-4-fluorophenol

Produkt 1

HCID 2872085-Fluoro-2(3H)-benzoxazoloneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-amino-4-fluorophenol (40.5 g, 0.32 mole) in 400 ml tetrahydrofuran, at 0° C., was added dropwise trichloromethyl chloroformate (44.8 ml, 0.32 mole). The reaction mixture was allowed to warm up to room temperature Stirring was continued for 2 hours. Then, the reaction mixture was poured onto ice and the organic substance was extracted with ethyl acetate (500 ml×3). The combined extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate and concentrated to yield 44.3 g of the title compound as brown solids.

Aufarbeitung

  1. additionThen, the reaction mixture was poured onto ice
  2. extractionthe organic substance was extracted with ethyl acetate (500 ml×3)
  3. washThe combined extracts were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8e5be6161f1f44a3846f193d6ffaae4e
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05086062

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