6-chloro-7-fluoro-2,3-diphenylquinoxaline synthesis

6synthesis methods

Product Name:6-chloro-7-fluoro-2,3-diphenylquinoxaline
CAS Number:218456-76-9
Molecular formula:C20H12ClFN2
Molecular Weight:334.77

134-81-6 Synthesis

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6-chloro-7-fluoro-2,3-diphenylquinoxaline

218456-76-9
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Yield:218456-76-9 82%

Reaction Conditions:

with acetic acid for 2.5 h;Reflux;

Steps:

8 4.5.8. Synthesis of 2,3-diphenyl-6-chloro-7-fluoroquinoxaline (7d)

Intermediate compound 5 (0.2 g, 1.24 mmol) and benzil 6d (0.26 g, 1.24 mmol) were weighed and dissolved in 20 mL glacial acetic acid.
This mixture was refluxed for 2.5hr.
The completion of reaction was monitored by TLC.
The reaction mixture was cooled and poured into crushed ice.
The precipitated product was filtered off and washed with cold water.
The product was then purified by column chromatography using hexane: ethyl acetate as mobile phase.
The pure fractions obtained were dried and concentrated to obtain white solids of product 7d. (yield 82%, m.p. 110-112 °C).
¹H NMR (400 MHz, CDCl₃), δ ppm, 7.3381-7.2488 (m, 6H, Ar-3,4,5-H at C-2 and C-3), 7.441-7.411 (m, 4H, Ar-2,6-H at C-2 and C-3), 7.8824 (d, J = 9.28, -H at C-5), 8.1930 (d, J = 7.6, -H at C-8).
¹³C NMR (400 MHz, CDCl₃), δ ppm, 113.66, 113.87, 125.44, 125.66, 128.38, 129.18, 129.27, 129.78, 129.81, 130.38, 138.38, 138.53, 138.46, 140.50, 140.61, 153.73, 153.76, 154.39, 156.93, 159.46.
Mass (ESI), C₂₀H₁₂ClFN₂, M⁺ and [M+2]⁺ peaks were found at 334 and 336, respectively.