Synthesis
General procedure for the synthesis of 2-bromobenzyl ketone from 2-bromo-diphenylmethanol: In a pre-dried oven-dried Schlenk tube, 2-bromo-diphenylmethanol (69.0-199.5 mg, 0.5 mmol), CuI (10 mol%), 1,10-phenanthroline (20 mol%), and K3PO4 (2 mmol) were sequentially added, followed by injection of dioxane ( 2 mL). The reaction system was stirred at room temperature and under air atmosphere, and subsequently transferred to an oil bath at 80 °C to heat the reaction for 7-48 h. The reaction was carried out by thin layer chromatography (TLC). The reaction process was monitored by thin layer chromatography (TLC) until the reaction was complete. Upon completion of the reaction, the mixture was cooled to room temperature and quenched with aqueous NH4Cl, followed by extraction with CH2Cl2 (3 × 10 mL). The organic phases were combined, washed with saturated NaCl solution, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated under reduced pressure, and the resulting crude product was further purified by silica gel column chromatography (eluent: mixed system of petroleum ether/ethyl acetate) to finally obtain the target product 2-bromobenzophenone in 61-97% yields.
References
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[2] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2059 - 2074
[3] Tetrahedron Asymmetry, 1992, vol. 3, # 7, p. 841 - 844
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 208 - 212
[5] Organic Letters, 2006, vol. 8, # 15, p. 3379 - 3381
