p-Fluoronitrobenzene → N,N-diethyl-3-(4-nitrophenoxy)propan-1-amine

Temperatur

0 °C

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%).

1. customthe ice-bath is removed
2. stirringThe reaction mixture is stirred at room temperature for 15 min
3. customThe dark green reaction mixture is quenched with ice-water (300 mL)
4. extractionextracted with EtOAc (2×200 mL)
5. washThe combined organic extracts are washed with water (2×300 mL) and brine (1×300 mL)
6. dry with materialdried over anhydrous Na2SO4
7. customThe oily brown residue obtained
8. customafter evaporation
9. customis purified by chromatography, (silica gel, 1:4 MeOH:CHCl3)

ORD-Eintrag

ord-b8a7013060c64ea0a72ae1347253d224

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07098236B2