Cesium carbonate → N-ethyl-5-(furan-3-yl)-2-methylaniline

HRID 1964015

Reaktionsgleichung

Reaktionsgleichung von HRID 1964015
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[NH:7][CH2:8][CH3:9].[O:12]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH2:8]([NH:7][C:6]1[CH:10]=[C:2]([C:14]2[CH:15]=[CH:16][O:12][CH:13]=2)[CH:3]=[CH:4][C:5]=1[CH3:11])[CH3:9]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 27739962-(Furan-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 437296995-bromo-N-ethyl-2-methylaniline

Produkt 1

HCID 66877311N-ethyl-5-(furan-3-yl)-2-methylanilineAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

0.69 g (3.20 mmol) of 5-bromo-N-ethyl-2-methylaniline and 0.93 g (4.80 mmol) of 3-furan boronic acid pinacol ester were dissolved in 7 mL of THF. 1.56 g (4.80 mmol) of cesium carbonate and 370 mg (0.32 mmol) of tetrakis(triphenyl phosphine)palladium(0) were added thereto and heated under reflux for 22 hours. After completion of the reaction, filtration was conducted, and the filtrate was condensed. The resulting crude product was separated and purified using silica gel column chromatography to give N-ethyl-5-(furan-3-yl)-2-methylaniline (yield: 98%).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for 22 hours
  3. customAfter completion of the reaction, filtration
  4. customcondensed
  5. customThe resulting crude product was separated
  6. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-6f317208b33b4f2a8539517b604f631b
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415479B2

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