Methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate → 6-Chloro-4-nitroisobenzofuran-1(3H)-one

HRID 1467708Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467708
BrC[C:3]1[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]([Cl:16])=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6]>O1CCOCC1.O>[Cl:16][C:10]1[CH:9]=[C:4]2[C:3]([CH2:8][O:7][C:5]2=[O:6])=[C:12]([N+:13]([O-:15])=[O:14])[CH:11]=1

Komponenten

4

Edukt 1

HCID 67258857Methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate

Produkt 1

HCID 672581206-Chloro-4-nitroisobenzofuran-1(3H)-oneAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(bromomethyl)-5-chloro-3-nitrobenzoate (7 g, 22.8 mmol) in 1,4-dioxane (50 mL) and water (50 mL) was heated to reflux for 4 days. Dioxane was removed under reduced pressure. The residue was extracted with EtOAc (300 mL×4). The combined organic layers were washed with brine, dried over Na2SO4, and concentrated to give crude product, which was purified by silica gel chromatography (petroleum ether to petroleum ether/EtOAc=5:1) to give the title compound (4 g, yield 82%) as a white solid.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 4 days
  3. customDioxane was removed under reduced pressure
  4. extractionThe residue was extracted with EtOAc (300 mL×4)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customto give crude product, which
  9. customwas purified by silica gel chromatography (petroleum ether to petroleum ether/EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-564b9f99dac14f18b4ae225e8596bbdf
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999987B2

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