Synthesis
General method: 8-quinoline methanol was dissolved in anhydrous DMSO (10 v/v), 1 equivalent of polymer bromide was added, and the reaction mixture was stirred at room temperature for the indicated time (see Table 1). Upon completion of the reaction, the mixture was filtered and the polymer bed was washed with DMSO. The DMSO layers were combined and the reaction was quenched with an ice-water mixture and subsequently extracted with ether. The ether layer was washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated to give pure 8-quinolinecarboxaldehyde. All products were structurally confirmed by nuclear magnetic resonance (NMR) and mass spectrometry (MS).
References
[1] Tetrahedron Letters, 2011, vol. 52, # 51, p. 6971 - 6973
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 10, p. 3480 - 3484
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 31, p. 9084 - 9087
[4] Angew. Chem., 2016, vol. 128, # 31, p. 9230 - 9233,4
