[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[CH2:5]CN.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:19][CH:20]=[CH:21][C:22]#[C:23][C:24]([CH3:27])([CH3:26])[CH3:25].[CH3:28][N:29](C)C=O>>[CH3:25][C:24]([CH3:27])([CH3:26])[C:23]#[C:22]/[CH:21]=[CH:20]/[CH2:19][N:29]([CH2:5][C:4]1[CH:8]=[CH:9][C:10]([F:11])=[C:2]([Br:1])[CH:3]=1)[CH3:28]N-(3-bromo-4-fluorobenzyl)methylamine (4.00 g; 18.3 mmol) and sodium carbonate (2.78 g; 26.3 mmol) were added to N,N-dimethylformamide (35 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (3.51 g; 17.5 mmol) in N,N-dimethylformamide (15 ml) was added dropwise. The mixture was stirred for 4 hours at room temperature, and the mixture was poured into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and then with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=10:1), to thereby yield 2.54 g of the target compound as orange oily matter (yield: 42.9%).
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