反応 #49763

反応方程式

hydrochloric acid

Methyl N-(2-fluoro-4-chloro-hydroxyphenyl)carbamate

cyclohexyl p-toluenesulfonate

potassium hydroxide

→

2-fluoro-4-chloro-5-cyclohexyloxyaniline

収率 25.6%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   その他After completion of the reaction
2. 2
   温度the reaction solution was cooled to room temperature
3. 3
   抽出the mixture was extracted with ethyl acetate (20 ml×3)
4. 4
   洗浄washed with water
5. 5
   乾燥a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
6. 6
   その他The drying agent was removed by filtration
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   その他to obtain a etude product
9. 9
   その他The product was isolated
10. 10
    その他purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1)

実験手順

Methyl N-(2-fluoro-4-chloro-hydroxyphenyl)carbamate (2.03 g, 9.23 mmol), cyclohexyl p-toluenesulfonate (2.51 g, 9.85 mmol) and N,N-dimethylformamide (30 ml) were charged into a 100 cc round-bottom flask, and then potassium hydroxide (1.0 g, 17.8 mmol) in a powder form was added thereto. The mixture was stirred for 4 hours on an oil bath at 80° C. After completion of the reaction, the reaction solution was cooled to room temperature, 1N hydrochloric acid (100 ml) was added thereto, and the mixture was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was distilled off under reduced pressure to obtain a etude product. The product was isolated and purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1) to obtain 2-fluoro-4-chloro-5-cyclohexyloxyaniline (574 mg, 2.36 mmol, 264 yield) and the unreacted starting material, methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (1.22 g, 5.54 mmol, 60% recovery ratio). The spectral data and the like are as shown in Reference Example 11.

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