1,3-Dibromopropane → HCID 86686569, Verbindung

HRID 1528089Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528089
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][C:14]([O:16][CH3:17])=[O:15].Br[CH2:19][CH2:20][CH2:21]Br.[Cl-].[NH4+]>CN(C=O)C>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[C:13]1([C:14]([O:16][CH3:17])=[O:15])[CH2:21][CH2:20][CH2:19]1

Komponenten

6

Edukt 4

HCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 86686570HCID 86686570, Verbindung

Produkt 1

HCID 86686569HCID 86686569, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of sodium hydride (9.49 g) in DMF (75 mL) was added dropwise a solution of methyl (2-fluoro-6-nitrophenyl)acetate (23 g) and 1,3-dibromopropane (13.1 mL) in DMF (15 mL) at 0° C. The reaction mixture was stirred at room temperature for 4 hr, cooled to 0° C. Saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (11.3 g).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-823b249abc8e43acad509323b50b7815
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090586B2

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