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ChemicalBook CAS DataBase List 5-BROMOMETHYL-3-(4-FLUORO-PHENYL)-ISOXAZOLE
5262-25-9

5-BROMOMETHYL-3-(4-FLUORO-PHENYL)-ISOXAZOLE synthesis

5synthesis methods
-

Yield:5262-25-9 75%

Reaction Conditions:

with sodium hydrogencarbonate in dichloromethane;water at 0; for 24 h;

Steps:

4.2. General procedure for the synthesis of 3-aryl-5-(bromomethyl)isoxazoles 3

General procedure: Compounds 3 were prepared according to slightly modified published procedure [15]. A mixture of propargyl bromide (3-3.5 mmol), saturated aq. NaHCO3 (2 mL) and DCM (1-2 mL) was added dropwise to the solution of benzohydroximinoyl chloride 2 (1 mmol) in dichloromethane (DCM) (1-2 mL) at 0 °C. The reaction mixture was stirred for 1 d (TLC control, light petroleum/ethyl acetate 10:1 (v/v)). Then the organic layer was separated, the inorganic layer was extracted with DCM, the combined organic phase was dried (Na2SO4) and concentrated under reduced pressure. The resulted solid was crystallized from hexanes or purified by column chromatography on silica gel with light petroleum/ethyl acetate (8:1, v/v) as an eluent.

References:

Serebryannikova, Anna V.;Galenko, Ekaterina E.;Novikov, Mikhail S.;Khlebnikov, Alexander F. [Tetrahedron,2021,vol. 88,art. no. 132153]

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