[F:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][CH:3]=1.BrN1C(=O)CCC1=O.N1C=CC=CC=1.N1([CH:30]=[CH:31][C:32]([O:34][CH3:35])=[O:33])CCCC1>C(Cl)(Cl)Cl.Cl.O.C(N(CC)CC)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][O:8][N:7]=2)=[CH:4][CH:3]=1To a solution of 1.05 g of 4-fluorobenzaldoxime (Beil. 7, I 132d, II 177d, III 863c) in 15 mL of chloroform were added 1.35 g of N-bromosuccinimide (NBS) and 0.04 mL of pyridine; the resulting mixture was stirred at r.t for 4 h under nitrogen atmosphere. After cooling at 0° C., 1.75 g of methyl β-pyrrolidinoacrylate (prepared as described in U.S. Pat. No. 4,144,047) and 1.26 mL of triethylamine were added and the suspension was stirred at r.t. for 18 h. The reaction mixture was diluted with 20 mL of 2 N hydrochloric acid, 20 mL of water; the organic layer was separated, washed again with 2 N hydrochloric acid and water, dried (sodium sulphate), and evaporated to dryness in vacuo. The crude was purified by flash chromatography (toluene-dichloromethane 1:9) to afford the title compound (47%) as an oil.
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