Cesium carbonate → 1-Bromo-4-(2,4-difluorophenoxy)-2-fluoro-5-nitrobenzene

HRID 633522

Reaktionsgleichung

Reaktionsgleichung von HRID 633522
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[F:12].C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[OH:27]>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[O:27][C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[F:19].[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:27][C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[F:19])=[CH:4][C:3]=1[F:12]

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 2230781-Bromo-2,4-difluoro-5-nitrobenzene

Produkt 2

HCID 904159951-Bromo-4-(2,4-difluorophenoxy)-2-fluoro-5-nitrobenzeneHCID 904186191-Bromo-2-(2,4-difluorophenoxy)-4-fluoro-5-nitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

A mixture of 1-bromo-2,4-difluoro-5-nitrobenzene (0.5 g, 2.10 mmol) and cesium carbonate (0.685 g, 2.10 mmol) in DMSO (10.50 mL) was treated dropwise with 2,4-difluorophenol (0.273 g, 2.10 mmol), stirred for 60 minutes at ambient temperature and partitioned between ethyl acetate and water, adjusting the pH to 6 with 1 M HCl. The organic layer was washed with water, saturated aqueous sodium chloride, dried (MgSO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-30% ethyl acetate in heptanes) afforded the title compound and 1-bromo-4-(2,4-difluorophenoxy)-2-fluoro-5-nitrobenzene as an inseparable mixture (0.59 g, 81%).

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 0-30% ethyl acetate in heptanes)

Quellen und Nachweise

ORD-Eintrag
ord-5e93caf2891d47e6b8f113ebe17841b7
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321764B2

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