[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.O>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][O:7][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)=[CH:4][CH:3]=1
To a solution of 4-bromobenzyl alcohol (25 g, 130 mmol) in N,N-dimethyl formamide (125 mL) was added potassium tert-butoxide (15.8 g, 141 mmol) at room temperature, which was stirred at 54° C. for 10 minutes. To this reaction solution was added 2-fluoropyridine (15 mL, 154 mmol) at from 40° C to 58° C, which was stirred further at 65° C for 30 minutes. The reaction solution was allowed to room temperature, and water and ethyl acetate were added to carry out liquid separation. The aqueous layer was extracted further with ethyl acetate (twice). The ethyl acetate layers were combined, washed with water (three times) and sodium chloride water (once), dried over anhydrous magnesium sulfate and then filtered. The filtrate thereof was concentrated under a reduced pressure. To the residue was added diethyl ether, and concentrated under a reduced pressure to obtain the title compound (34 g) as a crude product.
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