5-CHLORO-BENZOOXAZOLE-2-CARBOXYLIC ACID METHYL ESTER Chemical Properties

Melting point:

124 °C

Boiling point:

309.1±34.0 °C(Predicted)

Density 

1.416

storage temp. 

Sealed in dry,Room Temperature

pka

-1.88±0.10(Predicted)

Appearance

Off-white to light yellow Solid

5-CHLORO-BENZOOXAZOLE-2-CARBOXYLIC ACID METHYL ESTER Usage And Synthesis

Synthesis

Catalyst (9.9 mg, 0.025 mmol, 5 mol%), potassium tert-butoxide (0.0672 g, 0.6 mmol), DMF (3.0 mL), and 5-chlorobenzoxazole (76.79 mg, 0.5 mmol) were added to the reaction flask under argon protection. The reaction mixture was stirred at 80 °C for 18 h under carbon dioxide atmosphere at atmospheric pressure. Upon completion of the reaction, the system was cooled to 65 °C, followed by the addition of iodomethane (93 μL, 1.5 mmol) and continued stirring at 65 °C for 1 hour. At the end of the reaction, the system was cooled to room temperature and the reaction was quenched with deionized water. The reaction mixture was extracted with ethyl acetate, and the organic phases were combined and purified by column chromatography (Expanding agent: ethyl acetate/petroleum ether, 1:10, v/v). The target product methyl 5-chlorobenzoxazole-2-carboxylate was finally obtained in 82% yield.

References

[1] Organic Letters, 2010, vol. 12, # 15, p. 3567 - 3569
[2] Green Chemistry, 2018, vol. 20, # 5, p. 989 - 996
[3] Patent: CN106565623, 2017, A. Location in patent: Paragraph 0038
[4] Green Chemistry, 2013, vol. 15, # 3, p. 635 - 640

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