Synthesis
1-Bromo-2-(2,2-diethoxyethoxy)benzene (0102-3) (3.33 g, 11.56 mmol, 1.0 eq.) was used as a feedstock and dissolved in dichloroethane (DCE) (60 mL). Subsequently, polyphosphoric acid (PPA) (11.72 g, 34.68 mmol, 3.0 equiv) was added. The air in the round-bottomed flask was displaced three times by nitrogen, and then the reaction was refluxed for 3 h at 83 °C. After completion of the reaction, dichloromethane (100 mL) was added to the reaction mixture and washed with deionized water (100 mL x 3). The organic phase was dried with anhydrous sodium sulfate and subsequently concentrated. Finally, purification by silica gel column chromatography (eluent: 100% petroleum ether) afforded the light yellow solid product 7-bromobenzofuran (1.336 g, yield: 58%).
References
[1] Patent: US6353008, 2002, B1. Location in patent: Page column 38
[2] Patent: CN108658908, 2018, A. Location in patent: Paragraph 0160; 0162
[3] Patent: WO2007/117560, 2007, A2. Location in patent: Page/Page column 140-141
[4] Heterocyclic Communications, 2010, vol. 16, # 4-6, p. 249 - 252
[5] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 7, p. 2007 - 2017