Reaktion #11602

Reaktionsgleichung

1-fluoro-4-nitrobenzene

3-diethylamino-1-propanol

potassium tert-butoxide

→

compound

Ausbeute 71.2%

Diethyl-[3-(4-nitro-phenoxy)-propyl]-amine

Ausbeute 71.2%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe ice-bath is removed
2. 2
   workup.STIRRINGThe reaction mixture is stirred at room temperature for 15 min
3. 3
   SonstigeThe dark green reaction mixture is quenched with ice-water (300 mL)
4. 4
   Extraktionextracted with EtOAc (2×200 mL)
5. 5
   WaschenThe combined organic extracts are washed with water (2×300 mL) and brine (1×300 mL)
6. 6
   Trocknendried over anhydrous Na2SO4
7. 7
   SonstigeThe oily brown residue obtained
8. 8
   Sonstigeafter evaporation
9. 9
   Sonstigeis purified by chromatography, (silica gel, 1:4 MeOH:CHCl3)

Vorschrift

A solution of 3-diethylamino-1-propanol (2.97 mL, 20 mmol) in THF (40 mL) at 0° C. is treated potassium tert-butoxide (2.36 g, 1.05 equiv.) in one portion. The reaction mixture is stirred at 0° C. for 5 min during which time it becomes reddish brown. Neat 1-fluoro-4-nitrobenzene (2.82 g, 1 equiv.) is added dropwise and the ice-bath is removed. The reaction mixture is stirred at room temperature for 15 min. The dark green reaction mixture is quenched with ice-water (300 mL), and extracted with EtOAc (2×200 mL). The combined organic extracts are washed with water (2×300 mL) and brine (1×300 mL) and dried over anhydrous Na2SO4. The oily brown residue obtained after evaporation, is purified by chromatography, (silica gel, 1:4 MeOH:CHCl3) to give the named compound as a brown oil (3.59 g, 71%).

Quelle