Iodoethane → (4-Bromo-2-tert-butylphenyl)diethylamine

HRID 1698394Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698394
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][CH3:10])=[C:4]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:3]=1.[H-].[Na+].I[CH2:18][CH3:19].[Cl-].[NH4+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:18][CH3:19])[CH2:9][CH3:10])=[C:4]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:3]=1

Komponenten

6

Edukt 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 66671970HCID 66671970, Verbindung

Produkt 1

HCID 66671963(4-Bromo-2-tert-butylphenyl)diethylamineAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

5 g (20 mmol) of (4-bromo-2-tert-butylphenyl)-ethylamine are dissolved, under a stream of nitrogen, in 200 ml of DMSO. After cooling to 0° C., 1.7 g (43 mmol) of sodium hydride are added slowly. After 30 minutes, 3.4 ml (43 mmol) of iodoethane are added and the mixture is then brought back to ambient temperature and stirred for an entire weekend. It is then poured into a saturated solution of ammonium chloride and extracted twice with diethyl ether. The organic phase is washed with water and then dried and concentrated to dryness. The residue is purified by flash chromatography (95/5 heptane/EtOAc). 3.6 g of (4-bromo-2-tert-butylphenyl)diethylamine are obtained in the form of a yellow oil (yield=63%).

Aufarbeitung

  1. customis then brought back to ambient temperature
  2. extractionextracted twice with diethyl ether
  3. washThe organic phase is washed with water
  4. customdried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by flash chromatography (95/5 heptane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-e418f9606d294fcda0bf55addd72f14d
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163952B2

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