Downstream synthetic route of 189035-22-1

189035-22-1 6-Bromo-2,3-dihydrobenzofuran 11252616, abenzofuran compound, is more and more widely used in various fields.

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.189035-22-1,6-Bromo-2,3-dihydrobenzofuran,as a common compound, the synthetic route is as follows.

The title compound was prepared according to procedures reported in the literature and known by persons skill in the art, using 6-bromo-2,3-dihydro-1-benzofuran (1 g, 5.03 mmol) as starting material. In a preferred method, 6-bromo-2,3-dihydro-1-benzofuran (1 g, 5.03 mmol) in toluene (10 mL) was degassed for 30 min. To this solution, 1-ethoxyvinyl tributyltin (2.012 g, 5.53 mmol) and bis(triphenylphosphine)palladium dichloride (0.35 g, 0.50 mmol) were added at rt and stirred for 16 hours at 90 C. The reaction mixture was cooled to rt and filtered through celite. After evaporation of the solvent, 6 N HCl solution in water (10 mL) was added and the mixture was stirred for 1 hour at rt. It was concentrated and neutralized with sat. NaHCO3. The desired product was extracted with DCM (50 mL), dried over Na2SO4 and concentrated. The crude product was purified by flash chromatography to give the title compound. Yield: 73.7% (0.6 g, pale yellow solid). 1H NMR (400 MHz, DMSO-d6): delta 7.48 (d, J = 7.64 Hz, 1H), 7.37-7.35 (d, J = 7.68 Hz, 1H), 7.26 (s, 1H), 4.58 (t, J = 8.76 Hz, 2H), 3.24 (t, J = 8.76 Hz, 2H), 2.53 (s, 3H). LCMS: (Method A) 163.2 (M+H), Rt. 3.01 min, 97.60% (Max)., 189035-22-1

189035-22-1 6-Bromo-2,3-dihydrobenzofuran 11252616, abenzofuran compound, is more and more widely used in various fields.

Reference£º
Patent; ASCENEURON S. A.; QUATTROPANI, Anna; KULKARNI, Santosh S.; GIRI, Awadut Gajendra; KOEK, Johannes Nicolaas; (64 pag.)WO2017/144635; (2017); A1;,
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