Water → 2-Methoxy-1-nitro-4-vinylbenzene

HRID 419460Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 419460
[CH3:1][O:2][C:3]1[CH:8]=[C:7](Br)[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].O.[CH2:14](O)[CH2:15]C>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH:14]=[CH2:15])[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11]

Komponenten

5

Edukt 3

HCID 962WaterHCID 10311-PropanolHCID 117464905-Bromo-2-nitroanisole

Produkt 1

HCID 536287222-Methoxy-1-nitro-4-vinylbenzeneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Katalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To 5-bromo-2-nitrophenyl methyl ether (8.0 g, 34.47 mmol) in 80 mL of n-propanol was added, PdCl2(dppf)*DCM (0.5 g, 0.69 mmol), potassium ethenyl(trifluoro)borate (6.47 g, 48.3 mmol), and TEA (3.48 g, 34.47 mmol). The mixture was heated to 100° C. for 3 h. The mixture was poured into 250 mL of H2O and extracted with DCM, dried (Na2SO4), filtered, and rotovaped down, and purified by flash chromatography to give the title compound of step B (3.58 g, 19.98 mmol, 58%). 1H NMR (400 MHz, CDCl3) δ ppm 7.82-7.87 (m, 1H), 7.02-7.07 (m, 2H), 6.70 (dd, J=17.58, 10.80 Hz, 1H), 5.87 (d, J=17.58 Hz, 1H), 5.46 (d, J=10.99 Hz, 1H), 3.97 (s, 3H).

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. custompurified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5d314b0e4aae41de8b67b93189d98378
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08093239B2

Notizen zur Reaktion

Wird geladen…