OS(O)(=O)=O.[N+:6]([O-:9])(O)=[O:7].OS(O)(=O)=O.[CH3:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=1)=[O:17]>[N+]([O-])(O)=O>[CH3:15][C:16]([C:18]1[CH:19]=[C:20]([Cl:24])[CH:21]=[CH:22][C:23]=1[N+:6]([O-:9])=[O:7])=[O:17]65% HNO3 (80 ml) was stirred at −5° C.±1° C. and 98% H2SO4 (10 mix 10) was added dropwise. To the stirring solution of HNO3/H2SO4 was added 3-chloroacetophenone (54) (12.0 g, 77.6 mmol). The mixture was stirred at −5□±1□ for 3 h and poured into crushed ice, and extracted with CH2Cl2. The extract was dried over MgSO4 and evaporated. The crude product was purified by column chromatography (silica gel, n-hexane/EtOAc=15:1) to give 55 as yellow solid (9.3 g, 46.6 mmol). Yield: 55.8%; mp 47-49° C.; 1H-NMR (CDCl3, 200 MHz): δ 2.48 (s, 3H), 7.32 (d, J=2.4 Hz, 1H), 7.49 (dd, J=8.8, 2.2 Hz, 1H), 8.00 (d, J=8.8 Hz, 1H); 13C-NMR (CDCl3, 50 MHz) δ: 198.27, 143.78, 141.05, 139.44, 130.55, 127.36, 125.91, 30.06; Anal. Calcd for C8H6ClNO3: C, 48.14; H, 3.03; N, 7.02.
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