ChemicalBook CAS DataBase List Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester

Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester synthesis

7synthesis methods

Product Name:Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester
CAS Number:775304-60-4
Molecular formula:C16H11FN2O3
Molecular Weight:298.27

1141475-82-2

393-52-2

Benzoic acid, 3-[5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl]-, Methyl ester

775304-60-4

GENERAL METHOD: 2 mmol of methyl (E)-3-(N'-hydroxycarbamoyl)benzoate was dissolved in 200 mL of acetone in a round-bottomed flask; subsequently, 0.35 g (2.5 mmol) of K2CO3 and 2.5 mmol of o-fluorobenzoyl chloride were added to the reaction mixture, and the reaction was stirred for 24 h at room temperature. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was treated with an appropriate amount of water and refluxed for 30 minutes. After the reaction mixture was cooled, the 1,2,4-oxadiazole product was collected by filtration and further purified by column chromatography to afford the target compound, methyl 3-(5-(2-fluorophenyl)-1,2,4-oxadiazol-3-yl)benzoate.

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775304-60-4
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Yield:775304-60-4 92%

Reaction Conditions:

in toluene at 5 - 130; for 22 h;

Steps:

6.7

44g of 3-(N-2-Fluorobenzoylcarbamimidoyl)-benzoic acid methyl ester in toluene (500 mL) was refluxed for 4h at 130 °C using Dean-Stark apparatus. The reaction mixture was stirred at 5 °C for 18h. The white precipitate was filtered off and the filtrate was concentrated, crystallized again in toluene. The desired oxadiazole (38g, 92% yield) was obtained as a white solid with 99% purity (LC/UV). ¹H-NMR (CDCl₃) S 8.91 (IH)₅ 8.38 (IH)₃ 8.15 (2H), 7.62 (2H)₃ 7.35 (2H)₃ 3.95 (3H).

References:

WO2007/117438,2007,A2 Location in patent:Page/Page column 261