반응 #49744

반응 방정식

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

3,4,5,6-tetrahydrophthalic anhydride

→

N-{2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyphenyl}-3,4,5,6-tetrahydrophthalimide

수율 98.0%

용매

acetic acid

반응 조건

후처리

1. 1
   온도heated for 5 hours
2. 2
   온도while refluxing
3. 3
   기타After completion of the reaction
4. 4
   추출The mixture was extracted with ethyl acetate (30 ml×3)
5. 5
   세척washed with water
6. 6
   건조a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate
7. 7
   기타The drying agent was separated by filtration
8. 8
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
9. 9
   기타the resulting pale brown oily substance was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1)

실험 절차

2-Fluoro-4-chloro-5-(2-methylcyclopentyl)oxyaniline (660 mg, 2.71 mmol), 3,4,5,6-tetrahydrophthalic anhydride (503 mg, 3.31 mmol) and acetic acid (10 ml) were charged into a 50 cc round-bottom flask, and heated for 5 hours while refluxing. After completion of the reaction, the reaction solution was cooled to room temperature, and poured into ice-water (100 ml). The mixture was extracted with ethyl acetate (30 ml×3), and 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 separated by filtration, the solvent was distilled off under reduced pressure, and the resulting pale brown oily substance was purified by silica gel column chromatography (development solvent: hexane/ethyl acetate=9/1) to obtain N-{2-fluoro-4-chloro-5-(2-methylcyclopentyl)oxyphenyl}-3,4,5,6-tetrahydrophthalimide (1.00 g, 2.65 mmol, 98% yield).

출처