Synthesis
2-(2,2-dibromovinyl)phenol (2.8 g, 10 mmol) was dissolved in tetrahydrofuran (30 mL) under nitrogen protection. Subsequently, cuprous iodide (I) (0.1 g, 0.5 mmol) and potassium phosphate (4.2 g, 20 mmol) were added. The reaction mixture was stirred at 80°C for 12 hours. After completion of the reaction, the mixture was poured into water (200 mL) and extracted with ethyl acetate (200 mL). The organic phases were combined, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by column chromatography (silica gel, eluent ethyl acetate/petroleum ether=1:20) to afford the target product 2-bromobenzofuran (1.8 g, 92% yield).
References
[1] Tetrahedron, 2011, vol. 67, # 33, p. 5913 - 5919
[2] Chemical Communications, 2011, vol. 47, # 37, p. 10476 - 10478
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 24, p. 4095 - 4101
[4] Organic and Biomolecular Chemistry, 2012, vol. 10, # 21, p. 4172 - 4178
[5] Chemistry - A European Journal, 2015, vol. 21, # 4, p. 1482 - 1487
