Trifluoroacetic acid → 2,5-Dichloro-4-fluorophenol

HRID 252163

Reaktionsgleichung

Reaktionsgleichung von HRID 252163
[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8].FC(F)(F)C(O)=O.[Cl:17]N1C(=O)CCC1=O>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([Cl:17])=[CH:6][C:7]=1[F:8].[Cl:17][C:3]1[C:2]([Cl:1])=[C:7]([F:8])[CH:6]=[CH:5][C:4]=1[OH:9]

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 31398ChlorosuccinimideHCID 757903-Chloro-4-fluorophenol

Produkt 2

HCID 35357602,5-Dichloro-4-fluorophenolAusbeute 42 %HCID 53414207HCID 53414207, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

3-Chloro-4-fluorophenol (500 mg, 3.4 mmol) was dissolved in acetonitrile (25 mL) and trifluoroacetic acid (500 mL) was added, followed by addition of N-chlorosuccinimide (456 mg, 3.4 mmol). The reaction was stirred at ambient temperature for 3 days and the volatiles were then removed in vacuo. The crude product was purified by chromatography on silica gel with EtOAc:isohexane (1:19, v/v) as eluent to afford of 3,6-dichloro-4-fluorophenol (261 mg, 1.4 mmol, 42%) and 2,3-dichloro-4-fluorophenol (153 mg, 0.8 mmol, 25%).

Aufarbeitung

  1. customthe volatiles were then removed in vacuo
  2. customThe crude product was purified by chromatography on silica gel with EtOAc:isohexane (1:19

Quellen und Nachweise

ORD-Eintrag
ord-cc3e2e9c40884568883490e677e959b9
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07868017B2

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