6-Bromo-2-methylquinoline

106-40-1

123-73-9

877-42-9

GENERAL METHOD: 4-Bromoaniline (1.50 mmol) and trans-2-butenal (1.00 mmol) were dissolved in 1.5 mL of ether (Et2O) in a reaction flask fitted with a magnetic stir bar, followed by the addition of silver(I)-exchanged montmorillonite K10 (0.50 g). After stirring for 5 min, the solvent was removed under vacuum to obtain a dry powder. The reaction mixture was heated at 120 °C for 3 hours. After the reaction mixture was cooled to room temperature, it was filtered through a short silica gel plug and the solid residue was washed well with dichloromethane (CH2Cl2). After removal of the solvent under vacuum, the crude product was purified by silica gel column chromatography, eluting using a solvent mixture of hexane/ethyl acetate (EtOAc) to give the final 6-bromo-2-methylquinoline (3a-3k). Note: For recycling/reuse studies, the crude product is separated by gravity filtration and the clay material is washed several times with dichloromethane (CH2Cl2), air-dried and weighed. The process is repeated for successive recycling/reuse reactions.