Potassium Carbonate → Methyl 5-(2-methoxyethoxy)-2-nitrobenzoate

HRID 871317Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871317
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][O:24][CH3:25]>CN(C=O)C.O>[CH3:25][O:24][CH2:23][CH2:22][O:1][C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 12922678Methyl 5-hydroxy-2-nitrobenzoate

Produkt 1

HCID 66639151Methyl 5-(2-methoxyethoxy)-2-nitrobenzoateAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To methyl 5-hydroxy-2-nitrobenzoate (1.08 g, 5.5 mmol) in DMF (50 mL) was added potassium carbonate (1.52 g, 11 mmol) followed by 1-bromo-2-methoxyethane (1.55 mL, 16.4 mmol) and the mixture heated at 60° C. overnight. After cooling to room temperature, the reaction was diluted with H2O, extracted with EtOAc, and the organic layer washed with H2O and brine, dried over MgSO4, filtered, concentrated in vacuo, and purified by column chromatography (12-100% EtOAc/hexanes) to give methyl 5-(2-methoxyethoxy)-2-nitrobenzoate (1.08 g, 4.2 mmol, 77%). 1H NMR (300 MHz, DMSO-d6) δ 8.13 (d, 1H), 7.31 (s, 1H), 7.29 (d, 1H), 4.29 (dd, 2H), 3.86 (s, 3H), 3.68 (dd, 2H), 3.31 (s, 3H); LC-MS (ESI) m/z 256 (M+H)+.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with EtOAc
  3. washthe organic layer washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography (12-100% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-a09f2adf1d874fe385db8b04fa616e14
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969587B2

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