ChemicalBook CAS DataBase List 5-(4-FLUOROPHENYL)ISOXAZOLE

5-(4-FLUOROPHENYL)ISOXAZOLE synthesis

7synthesis methods

Product Name:5-(4-FLUOROPHENYL)ISOXAZOLE
CAS Number:138716-37-7
Molecular formula:C9H6FNO
Molecular Weight:163.15

80151-28-6 Synthesis

80151-28-6
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138716-37-7
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651059-64-2 Synthesis

651059-64-2
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Yield: 34% ， 51%

Reaction Conditions:

with N-iodo-succinimide;tert-Butyl N-hydroxycarbamate;trifluorormethanesulfonic acid in 1,2-dichloro-ethane at 83; for 5 h;Sealed tube;

Steps:

5 Example 5Method for preparing isoxazole derivative, two kinds of isoxazole derivative obtained,Isoxazole derivative I is 5- (4-fluorophenyl) isoxazole, and isoxazole derivative II is 3- (4-fluorophenyl) isoxazole;
The preparation process is: adding propargyl alcohol derivative, halogen source and acid in a sealed tube,The reaction was carried out under the condition of heating and refluxing at 83 ° C, and hydroxylamine was added after the disappearance of the propargyl alcohol derivative was monitored by TLC.After 5 hours of reaction, saturated brine was added to quench the reaction. The organic phase was extracted with ethyl acetate and dried over anhydrous sodium sulfate.Concentration yields the isoxazole derivative, which can be purified by column chromatography to calculate the yield:The yield of isoxazole derivative I was 34%, the yield of isoxazole derivative II was 51%, and the total yield of isoxazole derivatives was 85%.Among them, propargyl alcohol, halogen source, hydroxylamine,The solvent and acid loading were 3- (4-fluorophenyl) prop-2-yn-1-ol (2 mmol), NIS (2.4 mmol), N-tert-butoxycarbonylhydroxylamine (2.2 mmol),Dichloroethane (35 mL) and trifluoromethanesulfonic acid (0.2 mmol).

References:

Shanghai Institute of Technology;Yin Yan;Guo Huifeng;Pan Wanyong;Zhang Qinglin;Pei Keke CN110483430, 2019, A Location in patent:Paragraph 0072-0077