반응 #49761

반응 방정식

hydrochloric acid

methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate

2-methylcyclopentyl p-toluenesulfonate

potassium hydroxide

→

2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline

수율 40.0%

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   workup.ADDITIONwas charged into a 50 cc round-bottom flask
2. 2
   온도while heating on an oil bath at 80° to 100° C
3. 3
   기타After completion of the reaction
4. 4
   추출the mixture was extracted with ethyl acetate (20 ml×3)
5. 5
   세척washed with a saturated aqueous solution of sodium chloride
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   기타The drying agent was removed by filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   기타to obtain a crude product (1.51 g)
10. 10
    기타The product was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=17/3)

실험 절차

A solution of methyl N-(2-fluoro-4-chloro-5-hydroxyphenyl)carbamate (1.53 g, 6.98 mmol) synthesized by the process described in Reference Example 3, 2-methylcyclopentyl p-toluenesulfonate (1.78 g, 6.99 mmol) and N,N-dimethylformamide (15 ml) was charged into a 50 cc round-bottom flask, and then potassium hydroxide (400 mg, 7.15 mmol) in a powder form was added thereto, followed by stirring for 7 hours while heating on an oil bath at 80° to 100° C. After completion of the reaction, the reaction solution was cooled to room temperature, 2N hydrochloric acid (50 ml) was added thereto, and the mixture was extracted with ethyl acetate (20 ml×3). The organic layers were combined, washed with 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 crude product (1.51 g). The product was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=17/3) to obtain 2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline as a colorless oily substance (666 mg, 2.73 mmol, 40% yield).

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