Diethyl Ether → (3-Bromo-phenyl)-cyclopropyl-methyl-amine

HRID 2377435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2377435
[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:11])[CH:9]=O)[CH:5]=[CH:6][CH:7]=1.[CH2:12]([Mg]Br)[CH3:13].CCOCC.C(OCC)(=O)C>O1CCCC1.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([N:8]([CH:9]2[CH2:13][CH2:12]2)[CH3:11])[CH:5]=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 12030886N-(3-Bromo-phenyl)-N-methyl-formamide2×HCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 21107154(3-Bromo-phenyl)-cyclopropyl-methyl-amineAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A stirred, cooled (0° C.) solution of N-(3-bromo-phenyl)-N-methyl-formamide (Intermediate 112, 2.6 g, 9.7 mmol) and titanium tetra-iso-propoxide (3.9 mL, 10.67 mmol) in tetrahydrofuran (40 mL) was treated with a 3M solution of ethyl magnesium bromide in ether (8.08 mL, 24.25 mmol) under argon and the resulting reaction mixture was allowed to warm to ambient temperature gradually and refluxed at 55° C. overnight. It was then cooled in an ice-bath, quenched with saturated aqueous ammonium chloride solution, filtered over celite and the aqueous phase was extracted with diethyl ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford an oil. Flash column chromatography over silica gel (230-400 mesh) using 1.5% ethyl acetate in hexane as the eluent afforded the title compound (0.321 g, 15%).

Aufarbeitung

  1. customthe resulting reaction mixture
  2. temperaturerefluxed at 55° C. overnight
  3. temperatureIt was then cooled in an ice-bath
  4. customquenched with saturated aqueous ammonium chloride solution
  5. filtrationfiltered over celite
  6. extractionthe aqueous phase was extracted with diethyl ether
  7. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customto afford an oil

Quellen und Nachweise

ORD-Eintrag
ord-c2f37b4cc9d840ad8f9aae26b30a7944
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07468391B2

Notizen zur Reaktion

Wird geladen…