31% |
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 100℃; for 5h; |
23.1
Into a 100 mL -necked round-bottom flask, was placed a solution of 2-fluorophenol (2.6 g, 23.19 mmoi, 1.00 equiv) in N,N-dimethylformamide (30 mL) and CuCl (2.2 g, 2.41 equiv). This was followed by the addition of sodium hydride (1.34 g, 55,83 mmol, 0.86 equiv) in portions and then l-fluoro-4-nitrobenzene (2.8 g, 19.84 mmol, 0.67 equiv), The resulting solution was stirred for 5 h at 100 °C in an oil bath and the resulting solution was diluted with water/ice. The aqueous mixture was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate,and concentrated under vacuum. The residue was loaded onto a silica gel column and elution with ethyl acetate/petroleum ether (1 : 100) gave 1.7 g (31 %) of l-(2-fluorophenoxy)-4-nitrobenzene as a light yellow solid. |
31% |
With sodium hydride; copper(l) chloride In N,N-dimethyl-formamide at 100℃; for 5h; |
23.1
Step 1. Into a 100 mL 3-necked round-bottom flask, was placed a solution of 2-fluorophenol (2.6 g, 23.19 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL) and CuCl (2.2 g, 2.41 equiv). This was followed by the addition of sodium hydride (1.34 g, 55.83 mmol, 0.86 equiv) in portions and then 1-fluoro-4-nitrobenzene (2.8 g, 19.84 mmol, 0.67 equiv). The resulting solution was stirred for 5 h at 100 °C in an oil bath and the resulting solution wasdiluted with water/ice. The aqueous mixture was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate,and concentrated under vacuum. The residue was loaded onto a silica gel column and elution with ethyl acetate/petroleum ether (1:100) gave 1.7 g (31%) of 1-(2-fluorophenoxy)-4-nitrobenzene as a light yellow solid. |
31% |
With sodium hydride; copper(l) chloride In N,N-dimethyl-formamide; mineral oil at 100℃; for 5h; |
23.1
Step 1 Into a 100 mL 3-necked round-bottom flask, was placed a solution of 2-fluorophenol (2.6 g, 23.19 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL) and CuCl (2.2 g, 2.41 equiv). This was followed by the addition of sodium hydride (1.34 g, 55.83 mmol, 0.86 equiv) in portions and then 1-fluoro-4-nitrobenzene (2.8 g, 19.84 mmol, 0.67 equiv). The resulting solution was stirred for 5 h at 100° C. in an oil bath and the resulting solution was diluted with water/ice. The aqueous mixture was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was loaded onto a silica gel column and elution with ethyl acetate/petroleum ether (1:100) gave 1.7 g (31%) of 1-(2-fluorophenoxy)-4-nitrobenzene as a light yellow solid. |
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With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide |
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With potassium carbonate In N,N-dimethyl-formamide for 8h; Inert atmosphere; Heating; |
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