5-(BROMOMETHYL)-3-(4-CHLOROPHENYL)ISOXAZOLE synthesis

6synthesis methods

Product Name:5-(BROMOMETHYL)-3-(4-CHLOROPHENYL)ISOXAZOLE
CAS Number:5300-92-5
Molecular formula:C10H7BrClNO
Molecular Weight:272.53

106-96-7 Synthesis

106-96-7
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$31.00/25g

28123-63-9
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5-(BROMOMETHYL)-3-(4-CHLOROPHENYL)ISOXAZOLE

5300-92-5
18 suppliers
$195.00/250mg

Yield:5300-92-5 89%

Reaction Conditions:

with 2-(2'-pyridyl)benzimidazole;copper diacetate;potassium carbonate in water at 20; for 3 h;Green chemistry;regioselective reaction;

Steps:

General procedure for the synthesis of isoxazoles from nitrile oxides and alkynes

General procedure: To a stirred solution of imidoyl chloride (1 mmol) and alkyne (1 mmol) in H2O (5 mL), pyridinyl benzimidazole (1 mol%), copper(II)acetate (1 mol%) and K2CO3 (2 mmol)were added. The resulting solution was stirred at room temperature for 3 h. After the completion of the reaction, it was diluted with water, and the solid off-white isoxazole product was filtered off. 3-(4-Chlorophenyl)-5-phenylisoxazole (1) White solid, m.p: 177-178 °C. IR (KBr): 3114 (m), 1612 (s), 1489 (s), 1446(s), 1425 (s), 1383 (s), 1093 (s), 1015 (s), 950 (s), 838 (s),815 (s), 760 (s), 693 (s), 517 (s) cm^-1. ¹H NMR (250 MHz,CDCl3): δ = 6. 80 (s, 1H), 7.44-7.52 (m, 5H), 7.79-7.88 (m,4H). ¹³C NMR (62.5 MHz, CDCl3): δ = 97.3, 125.8, 127.2,128.0, 128.2, 129.0, 129.2, 130.3, 136.0, 161.8, 168.3.Mas m/z (%) 257 (M++2, 2.8), 256 (M⁺+1, 7.5), 255 (M⁺,10.5), 105 (100.0), 77 (41.1). Anal. calcd. for C15H10ClNO (255.699): C 70.46 H 3.94; found: C 79.81, H 4.97.

References:

Khalifeh, Reza;Shahriarpour, Fatemeh;Sharghi, Hashem;Aberi, Mahdi [Journal of the Iranian Chemical Society,2018,vol. 15,# 4,p. 813 - 821]