Phenol → HCID 118093763, Verbindung

HRID 1056969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1056969
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1F.C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CS(C)=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Komponenten

7

Edukt 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 753658901-Bromo-2,4-difluoro-3-nitrobenzene

Produkt 1

HCID 118093763HCID 118093763, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of 1-bromo-2,4-difluoro-3-nitrobenzene (0.128 g, 0.538 mmol) [Combi-Blocks, AN-3334] and cesium carbonate (0.211 g, 0.646 mmol) in dimethyl sulfoxide (0.59 mL) was treated with phenol (0.0609 g, 0.647 mmol) and stirred at 20° C. for 3 h, after which time the reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated to give a crude oil. Purification by preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min) gave the desired product (57 mg, 34%) as a yellow solid.

Aufarbeitung

  1. customLayers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil
  7. customPurification by preparative LCMS (XBridge C18 column
  8. washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-a7fbb52642824da5ac8fec360011feae
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399640B2

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