[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9])[O:11][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1A mixture of 3-fluoro-4-nitrophenol (1.6 g, 10 mmol), 4-(2-chloroethyl)morpholine hydrochloride (1.9 g, 10 mmol), and potassium carbonate (5.5 g, 52 mmol) in acetone (50 mL) was heated to reflux with stirring for 16 hours. The mixture was cooled and evaporated under vacuum. The residue was partitioned between water (100 mL) and ethyl acetate (100 mL), and the organic phase was washed with water (100 mL) and brine (100 mL), was dried (MgSO4), and evaporated, providing 2.6 g, in 93% yield; 1H NMR (DMSO-d6) δ 2.47 (t, 4H, J=4.6), 2.71 (t, J=5.6 Hz, 2H), 3.57 (t, J=4.6, 4H), 4.25 (t, J=5.6 Hz, 2H), 6.99 (dd, J=9.3 Hz, J=2.7 Hz, 1H), 7.19-7.24 (m, 1H), 8.14 (t, J=9.3 Hz, 1H).
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