5-chloro-3-(4-methoxyphenyl)benzo[c]isoxazole synthesis

4synthesis methods

Product Name:5-chloro-3-(4-methoxyphenyl)benzo[c]isoxazole
CAS Number:728-22-3
Molecular formula:C14H10ClNO2
Molecular Weight:259.69

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5-chloro-3-(4-methoxyphenyl)benzo[c]isoxazole

728-22-3
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Yield:728-22-3 86%

Reaction Conditions:

with oxone in water;acetonitrile at 20; for 8 h;Green chemistry;chemoselective reaction;

Steps:

Oxidative Cyclization of 2-Aminoacylbenzenes 1; Typical Procedure

General procedure: Oxone (0.270 g, 0.44 mmol) was added to a solution of (E)-1-(2-aminophenyl)-3-(4-fluorophenyl)prop-2-en-1-one (1g) (0.106 g, 0.44mmol) in MeCN/H2O (2.5 mL/2.5 mL). The mixture was stirred at r.t. and the progress was monitored by TLC and GC-MS. After stirring for 24 h, H2O (150 mL) and CH2Cl2 (150 mL) were added. The organic layer was separated and the aq layer was extracted with CH2Cl2. The combined organic layers were washed with H2O, dried over Na2SO4, filtered and concentrated. The filtrate was evaporated and subjected to column chromatography on silica gel (n-hexane/EtOAc, 98:2) togive 2,1-benzisoxazole 3g.

References:

Chiarini, Marco;Del Vecchio, Luana;Marinelli, Fabio;Rossi, Leucio;Arcadi, Antonio [Synthesis,2016,vol. 48,# 18,art. no. SS-2016-E0249-FA,p. 3017 - 3030]