반응 #160613

반응 방정식

1,2,3-Trifluoro-5-methylbenzene

HNO3

→

title product

수율 85.0%

1,2,3-Trifluoro-5-methyl-4-nitrobenzene

수율 85.0%

용매

H2SO4

반응 조건

후처리

1. 1
   온도while maintaining the internal temperature below 20° C
2. 2
   workup.ADDITIONpoured onto ice (300 g)
3. 3
   추출the oily layer was extracted with CH2Cl2 (2×125 ml)
4. 4
   세척The organic layer was washed with water (2×200 ml), brine (200 ml)
5. 5
   건조dried (MgSO4)
6. 6
   기타evaporated
7. 7
   기타to obtain the crude product which
8. 8
   기타was purified over flash silica gel chromatography

실험 절차

1,2,3-Trifluoro-5-methylbenzene (40 mmol) was added to conc. H2SO4 (50 ml) at 0-5° C. Then the reaction mixture was slowly treated with conc. HNO3 (3.39 ml, 48.44 mmol, 90%) while maintaining the internal temperature below 20° C. The reaction mixture was stirred at room temperature for 16 h and poured onto ice (300 g) and the oily layer was extracted with CH2Cl2 (2×125 ml). The organic layer was washed with water (2×200 ml), brine (200 ml) and dried (MgSO4) and evaporated to obtain the crude product which was purified over flash silica gel chromatography to obtain the title product (6.5 g, 85%). 1H-NMR (300 MHz, CDCl3): δ 6.96 (septet, 1H), 2.39 (s, 3H). 19FNMR (CDCl3): δ −128.18, −141.50, −159.05.

출처