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With N-chloro-succinimide; In N,N-dimethyl-formamide;
2-Chloro-4-fluoro-6-nitroaniline 2-Chloro-4-fluoro-6-nitroaniline was prepared using an adaptation of the method of Mitchell, et al. (Mitchell, R. H. et al., J. Org. Chem. 44:4733 (1979)). To a solution of 4-fluoro-2-nitroaniline (500 mg, 3.2 mmol) in dry DMF (10 mL) under N2 was added dropwise a solution of N-chlorosuccinimide (426 mg, 3.2 mmol) in dry DMF (16 mL). The reaction was allowed to stir overnight. The solution was then poured into 100 mL H2 O and the resulting cloudy suspension extracted with 4*25 mL ethyl acetate. The combined organic phases were washed with 4*25 mL H2 O and 25 mL saturated NaCl solution and dried (MgSO4). The MgSO4 was vacuum filtered and the solvent rotary evaporated to yield a brown crystalline solid which was purified further by flash chromatography (2:1 hexanes:ethyl acetate) to yield 424 mg of an orange crystalline solid (69.5%) 1 H NMR (CDCl3) δ6.46 (br s, 2H, NH2), 7.42 (dd, JH5-3 =3 Hz, JH3-F =7.2 Hz, H-4), 7.85 (dd, JH5-3 =3 Hz, JH5-F =8.7 Hz, H-5)
With indium; acetic acid; In ethyl acetate; for 4.0h;Reflux; Inert atmosphere;
General procedure: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.
1-(4-fluoro-2-nitrophenyl)-5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
81%
With potassium phosphate; copper; In dimethyl sulfoxide; at 90℃; for 16h;
General procedure: A mixture of <strong>[881674-56-2]5-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde</strong> 1 (5.28 mmol), different o-fluoritro benzene 2 (6.33mmol), copper powder and K3PO4 (15.84 mmol) in anhydrous dimethyl sulfoxide (50ml) was heated to 90. After 16h, the reaction mixture was cooled to room temperature and filtered, the filtrate was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with water, dried over anhydrous Na2SO4, filtered and evaporated in vacuo. The crude product was purified on the silica gel to afford 3a-d as yellow solids.
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