반응 #342117
ord-3d0f3b3a5d104fabbe96ee66cebd9ef1
반응 방정식
반응 조건
후처리
- 1온도heated
- 2온도at reflux
- 3기타irradiated with light (100 W bulb) for 4 hours
- 4여과The reaction mixture was filtered
- 5농축concentrated
- 6workup.DISSOLUTIONThe residue was dissolved in THF (50 mL)
- 7여과filtered
- 8기타The solvent of the filtrate was evaporated
- 9기타The bright orange residue obtained
- 10추출extracted with ethyl acetate (2×25 mL)
- 11추출extracted with methylene chloride
- 12건조Both ethyl acetate solution and methylene chloride solution were dried over anhydrous Na2SO4 separately
- 13기타Evaporation of ethyl acetate solution
- 14기타afforded an orange oil which
- 15기타was recrystallized from hexane
실험 절차
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%).