C[Si]([N-:5][Si](C)(C)C)(C)C.[Li+].[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]#[N:16].Cl.[OH-].[Na+]>CCOCC.O>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[C:15]([NH2:5])=[NH:16]To a solution of lithium bis(trimethylsilyl)amide (1.0 M in tetrahydrofuran) was added a solution of 3-fluorobenzonitrile (2.5 g, Aldrich, USA) in 10 mL of anhydrous ether. After standing at room temperature for 2 h, the solution was cooled to 0° C. in an ice bath, and 28 mL of 3 M hydrochloric acid was added slowly. After stirring for 30 min, 100 mL of water was added and the ether layer was discarded. The aqueous layer was made basic with 2 M sodium hydroxide and extracted three times with chloroform. The chloroform layers were combined, dried over magnesium sulfate and concentrated in vacuo to yield 3-fluorobenzamidine (1.27 g) as a clear oil.
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