[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([Cl:12])=[N:7]2.C(=O)([O-])[O-].[K+].[K+].[F:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1>CC(C)=O>[Cl:12][C:6]1[CH:5]=[CH:4][C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[O:1][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([F:19])=[CH:21][CH:22]=2)[N:7]=15-Hydroxy-2-chloroquinoline (CAS 124467-35-2, 0.6 g, 3.0 mmol) was dissolved in 15 mL acetone and potassium carbonate (555 mg, 3.0 mmol) was added. Then 4-fluoro-benzylbromide (0.5 ml, 4.0 mmol) was added and the reaction mixture stirred for 18 hours at ambient temperature. The mixture was evaporated and the residue taken up in water and extracted (3×) with ethyl acetate. The combined organic phases were dried over sodium sulfate and evaporated. The residue was subjected to flash column chromatography on silica gel (heptane/ethyl acetate 90:10->80:20 gradient) to yield 2-chloro-5-(4-fluoro-benzyloxy)-quinoline as a white solid (420 mg, 44%), MS: m/e=289 (M+H+).
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