Nitric Acid → 1,2,3-Trifluoro-5-methyl-4-nitrobenzene
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([F:9])[C:3]=1[F:10].[N+:11]([O-])([OH:13])=[O:12]>OS(O)(=O)=O>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:11]([O-:13])=[O:12])=[C:4]([F:9])[C:3]=1[F:10]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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 cone. 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.