تفاعل #49763

معادلة التفاعل

hydrochloric acid

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

cyclohexyl p-toluenesulfonate

potassium hydroxide

→

2-fluoro-4-chloro-5-cyclohexyloxyaniline

المردود 25.6%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter completion of the reaction
2. 2
   درجة الحرارةthe reaction solution was cooled to room temperature
3. 3
   استخلاصthe mixture was extracted with ethyl acetate (20 ml×3)
4. 4
   غسيلwashed with water
5. 5
   تجفيفa saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
6. 6
   أخرىThe drying agent was removed by filtration
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   أخرىto obtain a etude product
9. 9
   أخرىThe product was isolated
10. 10
    أخرىpurified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1)

الإجراء التجريبي

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.

المصدر