Analyzing the synthesis route of 5-Chlorobenzo[d]oxazole-2(3H)-thione

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Chlorobenzo[d]oxazole-2(3H)-thione,belong benzoxazole compound

As a common heterocyclic compound, it belong benzoxazole compound,5-Chlorobenzo[d]oxazole-2(3H)-thione,22876-19-3,Molecular formula: C7H4ClNOS,mainly used in chemical industry, its synthesis route is as follows.,22876-19-3

General procedure: Phosphorus tribromide (89 muL, 0.11 mmol) was dropwisely added to a solution of commercial 2-phenethylbenzylalcohol (75 mg, 0.35 mmol) in dry THF (5 mL) at 0 C. After stirring at room temperature for 2h, the reaction mixture was extracted with EtOAc after quenching with water. The organic extract was washed with brine and dried over MgSO4. Evaporation of the filtrate provided crude 2-phenethylbenzyl bromide. Then, commercial 2-mercaptoimidazole (70 mg, 0.47 mmol), sodium hydride (22 mg, 0.55 mmol) and potassium iodide (78 mg, 0.47 mmol) was added to a solution of crude 2-phenethylbenzyl bromide in DMF (3 mL). After stirring at 100C overnight, the reaction mixture was quenched with water, extracted with EtOAc, washed with brine and dried over MgSO4 and evaporated. Purification of the residue by column chromatography on silica gel (hexane/EtOAc = 1/1) provided the title compound (44 mg, 0.15 mmol) as a colorless solid in 43% yield.

With the synthetic route has been constantly updated, we look forward to future research findings about 5-Chlorobenzo[d]oxazole-2(3H)-thione,belong benzoxazole compound

Reference£º
Article; Fukuda, Miwa; Sasaki, Tomomi; Hashimoto, Tomoko; Miyachi, Hiroyuki; Waki, Minoru; Asai, Akira; Takikawa, Osamu; Ohno, Osamu; Matsuno, Kenji; Bioorganic and Medicinal Chemistry Letters; vol. 28; 17; (2018); p. 2846 – 2849;,
Benzoxazole – Wikipedia
Benzoxazole | C7H5NO – PubChem