Water → 2-(2,6-Dibromo-pyridin-4-yloxy)-4-fluoro-benzoic acid methyl ester

HRID 1848920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1848920
[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([OH:12])[CH:3]=1.[Br:13][C:14]1[CH:19]=[C:18]([N+]([O-])=O)[CH:17]=[C:16]([Br:23])[N:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[CH3:9][O:8][C:6](=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([F:1])=[CH:3][C:4]=1[O:12][C:18]1[CH:17]=[C:16]([Br:23])[N:15]=[C:14]([Br:13])[CH:19]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 2775386Methyl 4-fluorosalicylateHCID 160387482,6-Dibromo-4-nitropyridine

Produkt 1

HCID 866428782-(2,6-Dibromo-pyridin-4-yloxy)-4-fluoro-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of methyl 4-fluoro-2-hydroxybenzoate (2.00 g), 2,6-dibromo-4-nitropyridine (3.65 g), and cesium carbonate (4.21 g) in N,N-dimethylformamide (100 mL) was heated to 55° C. for 16 hours, cooled, added to water, and extracted with 50% ethyl acetate in hexanes. The organic extract was washed with brine, dried over anhydrous sodium sulfate, filtered, concentrated and purified by flash column chromatography on silica gel using 30-50% ethyl acetate in hexanes.

Aufarbeitung

  1. temperaturecooled
  2. extractionextracted with 50% ethyl acetate in hexanes
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography on silica gel using 30-50% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-442f7271587641c594b49147de302eba
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08952157B2

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