Реакция #45776

Уравнение реакции

citric acid

Triethylamine

cyclobutanecarbonyl chloride

2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile

→

compound

Выход 85.0%

4-Amino-5-cyano-2-fluoro-6-methylbiphenyl-3-yl cyclobutanecarboxylate

Выход 85.0%

Растворители

acetonitrile

Условия реакции

Обработка

1. 1
   Другоеthe solvent was evaporated away under, reduced pressure
2. 2
   workup.ADDITIONEthyl acetate was added to the resulting residue
3. 3
   Промывкаby washing with saturated brine
4. 4
   СушкаThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Другоеthe solvent was evaporated away under reduced pressure

Методика

Under nitrogen atmosphere, 2-amino-5-phenyl-4-fluoro-3-hydroxy-6-methylbenzonitrile (I-41) (250 mg, 1.03 mmol) was dissolved in acetonitrile (0.10 ml), and cooled to 0° C. Triethylamine (244 μl, 1.75 mmol) and cyclobutanecarbonyl chloride (177 μl, 1.55 mmol) were dropwise added to the solution, followed by stirring at room temperature for 1 hour. 10% citric acid was added to the reaction liquid, and the solvent was evaporated away under, reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with saturated brine. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated away under reduced pressure. The resulting residue was subjected to silica gel column chromatography, and the eluate with ethyl acetate/hexane (1:4, v/v) gave the entitled compound (283 mg, 85%) as a white solid.

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