[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].[F:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[C:12](Cl)=[O:13].Cl.[CH2:21]1COCC1>>[F:8][C:9]1[CH:10]=[C:11]([C:12]([O:13][CH3:21])=[C:2]([C:1]#[N:5])[C:3]#[N:4])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1A solution of malononitrile (2.87 g, 0.044 mol) in dry THF (50 ml) was stirred at 0° C. under an argon atmosphere. NaH in paraffin oil (4.64 g, 0.116 mol) was added piece-wise to solution. 3-fluoro-5-methoxybenzoyl chloride (BA67, 0.029 mol) was dissolved in 50 ml dry THF and added slowly to reaction. Reaction was warmed to room temperature and stirred under argon for 24 hours. 1N HCl (200 ml) was slowly added, then reaction mixture was extracted with EtOAc. Organic phases were combined, dried with magnesium sulfate, then concentrated in vacuo to yield 2-((3-fluoro-5-methoxyphenyl)(methoxy)methylene)malononitrile (BA69).
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