Simple exploration of 64169-34-2

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With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.64169-34-2,5-Bromoisobenzofuran-1(3H)-one,as a common compound, the synthetic route is as follows.

A three-neck 5L round bottomed flask equipped with a stir bar, firestone valve, thermocouple, condenser andheating mantle was charged with tri-t-butyl phosphonium tetrafluoroborate (500 mg, 1.7 mmol), palladium (II) acetate(250 mg, 1.1 mmol) and 5-bromo-2-benzofuran-1(3H)-one (100 g, 470 mmol). DMF (1.9 L) was added to the flask, andthe mixture was degassed three times by alternating vacuum and nitrogen purge. Commercially available bromo(1,3-dioxolan-2-ylmethyl)zinc solution (1.0 L, 520 mmol) was added via canula and the mixture was again degassed threetimes. The mixture was then heated at 85 C for 5 h. Analysis by HPLC-MS indicated the reaction was not complete.The mixture was stirred at 85 C for 5 more h. The mixture was then allowed to return to room temperature for overnight.2-methyltetrahydrofuran (2.0 L) and brine were added, and the mixture was stirred for 5 min. The layers were separatedand the aqueous layer was extracted again with 2-methyltetrahydrofuran. The organic layers were combined, washedthree times with brine, dried over MgSO4,filtered, and concentrated. The resulting residue was purified by flash chromatography(1.5 kg silica cartridge), eluting with 0->20% ethyl acetate in dichloromethane to afford 5-(1,3-dioxolan-2-ylmethyl)-2-benzofuran-1(3H)-one. MS: m/z 221 (M+1)+.

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Reference£º
Patent; Merck Sharp & Dohme Corp.; WALSH, Shawn; PASTERNAK, Alexander; CATO, Brian; FINKE, Paul, E.; FRIE, Jessica; FU, Qinghong; KIM, Dooseop; PIO, Barbara; SHAHRIPOUR, Aurash; SHI, Zhi-Cai; TANG, Haifeng; (136 pag.)EP2755656; (2016); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem