2,3,5,6-Tetrafluorophenol → Diphenyl carbonate

HRID 1091424Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091424
[F-].[K+].F[C:4]1[C:9](F)=[CH:8][C:7](F)=[C:6](F)[C:5]=1[OH:13].F[C:15]1[CH:20]=[C:19](F)[CH:18]=[C:17](F)[C:16]=1[OH:23].FC1C(F)=CC=C(F)[C:26]=1[OH:33].BrC(Br)=O>CO.C1COCC1.CN(C)C=O>[O:13]([C:26]([O:23][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:15]=1)=[O:33])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:4]=1

Komponenten

9

Edukt 5

HCID 698582,3,5,6-TetrafluorophenolHCID 79057Carbonyl bromideHCID 5179882,3,6-TrifluorophenolHCID 5199742,4,6-TrifluorophenolHCID 522689Potassium Fluoride3×

Produkt 1

HCID 7597Diphenyl carbonate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittel2×HCID 6228DimethylformamideLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In scheme II above, the following abbreviations are used: KF is potassium fluoride; DMF is N,N-dimethylformamide; Ar2OH is either 2,3,5,6-tetrafluorophenol, 2,4,6-trifluorophenol or 2,3,6-trifluorophenol; THF is tetahydrofuran; MeOH is methanol. Commercially available bromoketone D is reacted with the appropriately substituted fluorophenol and potassium fluoride to give phenoxy ketone E. The ketone is then reduced with sodium borohydride to give the alcohol F, which is hydrogenated using palladium on carbon as catalyst to give the amino alcohol B′ (Ar2=fluoro-substituted phenyl).

Quellen und Nachweise

ORD-Eintrag
ord-4f6a14a8857f42a192f4c40f12dd5b61
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129381B2

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