Br.[Br:2][C:3]1[C:12]([OH:13])=[C:11]([CH3:14])[CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][C:7]([CH3:15])=[N:8]2.[O:16](S(C(F)(F)F)(=O)=O)[S:17]([C:20]([F:23])([F:22])[F:21])(=O)=[O:18]>ClCCl.N1C=CC=CC=1>[F:21][C:20]([F:23])([F:22])[S:17]([O:13][C:12]1[C:3]([Br:2])=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:14])[N:8]=[C:7]([CH3:15])[CH:6]=[CH:5]2)(=[O:18])=[O:16]To a stirred solution of 5-bromo-2,7-dimethylquinolin-6-ol-HBr (1.04 g, 3.1 mmol) in dichloromethane (50 mL) and pyridine (10 mL) was added Tf2O (1.1 mL, 6.2 mmol) at 0° C. The mixture was stirred at room temperature for 2 hours, quenched with slow addition of NaHCO3 solution at 0° C. The mixture was extracted with dichloromethane. The organic layer was washed with brine and dried with Na2SO4. Concentration gave 5-bromo-2,7-dimethylquinolin-6-yl trifluoromethanesulfonate as a brown solid.
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