تفاعل #342117
ord-3d0f3b3a5d104fabbe96ee66cebd9ef1
معادلة التفاعل
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةheated
- 2درجة الحرارةat reflux
- 3أخرىirradiated with light (100 W bulb) for 4 hours
- 4ترشيحThe reaction mixture was filtered
- 5تركيزconcentrated
- 6workup.DISSOLUTIONThe residue was dissolved in THF (50 mL)
- 7ترشيحfiltered
- 8أخرىThe solvent of the filtrate was evaporated
- 9أخرىThe bright orange residue obtained
- 10استخلاصextracted with ethyl acetate (2×25 mL)
- 11استخلاصextracted with methylene chloride
- 12تجفيفBoth ethyl acetate solution and methylene chloride solution were dried over anhydrous Na2SO4 separately
- 13أخرىEvaporation of ethyl acetate solution
- 14أخرىafforded an orange oil which
- 15أخرىwas recrystallized from hexane
الإجراء التجريبي
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%).