Reacción #342117

Ecuación de reacción

Morpholine

5-Fluoro-2-nitrotoluene

N-bromosuccinimide

benzoyl peroxide

HCl

→

yellow solid

Rendimiento 18.7%

4-(5-Fluoro-2-nitrobenzyl)morpholine

Rendimiento 18.7%

Disolventes

THF

CCl4

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaat reflux
3. 3
   Otroirradiated with light (100 W bulb) for 4 hours
4. 4
   FiltraciónThe reaction mixture was filtered
5. 5
   Concentraciónconcentrated
6. 6
   workup.DISSOLUTIONThe residue was dissolved in THF (50 mL)
7. 7
   Filtraciónfiltered
8. 8
   OtroThe solvent of the filtrate was evaporated
9. 9
   OtroThe bright orange residue obtained
10. 10
    Extracciónextracted with ethyl acetate (2×25 mL)
11. 11
    Extracciónextracted with methylene chloride
12. 12
    SecadoBoth ethyl acetate solution and methylene chloride solution were dried over anhydrous Na2SO4 separately
13. 13
    OtroEvaporation of ethyl acetate solution
14. 14
    Otroafforded an orange oil which
15. 15
    Otrowas recrystallized from hexane

Procedimiento

5-Fluoro-2-nitrotoluene (1.55 g, 10 mmol), N-bromosuccinimide (1.82 g, 10 mmol), and benzoyl peroxide (0.1 g, 0.4 mmol) were dissolved in CCl4 (50 mL), heated at reflux, and irradiated with light (100 W bulb) for 4 hours. The reaction mixture was filtered and concentrated. The residue was dissolved in THF (50 mL). Morpholine (1.9 g, 22 mmol) was added to the THF solution. The mixture was stirred at ambient temperature for 1 hour and then filtered. The solvent of the filtrate was evaporated. The bright orange residue obtained was then mixed with 5% HCl solution (30 mL) and extracted with ethyl acetate (2×25 mL). The aqueous layer was basified with NaOH solution to pH 8 and then extracted with methylene chloride. Both ethyl acetate solution and methylene chloride solution were dried over anhydrous Na2SO4 separately. Evaporation of ethyl acetate solution afforded an orange oil which was recrystallized from hexane:ether solution to yield 450 mg of a yellow solid, 4-(3-methyl-4-nitrophenyl)morpholine (18%), the by-product. Evaporation of methylene chloride solution afforded 660 mg of the desired compound, 4-(5-fluoro-2-nitrobenzyl)morpholine (27.5%).

Fuente