[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.C(N(CC)CC)C.N[CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1.C(O)C>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1An eggplant flask was charged with 5-bromo-2-fluoronitrobenzene (3.0 g, 13.6 mmol), triethylamine (1.66 g, 16.3 mmol), 4-aminotetrahydropyran (1.52 g, 15.0 mmol), and ethanol (60 mL), and this was heated to reflux with stirring for 2 hours. After concentration of the reaction mixture under reduced pressure, water (60 mL) was added and this was stirred as is at room temperature for 30 minutes. The precipitated crystals were filtered off and washed with water. The crystals obtained were dried at reduced pressure with heating to yield the title compound (3.55 g, 86% yield) as a reddish-orange solid.
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