CCCC[N+](CCCC)(CCCC)CCCC.[F-].[F:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([O:29][CH3:30])=[O:28])=[C:22]([C:31]#[C:32][Si](C)(C)C)[CH:21]=1>C(Cl)Cl.O>[C:31]([C:22]1[CH:21]=[C:20]([F:19])[CH:25]=[CH:24][C:23]=1[CH2:26][C:27]([O:29][CH3:30])=[O:28])#[CH:32]A solution of TBAF (1.0 M in THF; 2.0 mL, 2.0 mmol) was added to a stirred solution of methyl 2-(4-fluoro-2-((trimethylsilyl)ethynyl)phenyl)acetate (A49) (0.212 g, 0.802 mmol) in DCM (5 mL). After 2 minutes the resulting mixture was diluted with water (100 mL) and DCM (50 mL). The organic fraction was separated and adsorbed onto silica gel then purified using column chromatography (Biotage Isolera, 12 g SiO2 Cartridge, 0-20% EtOAc in petroleum benzine 40-60° C.) to give the title compound A50 as a brown oil (0.106 g, 69%); 1H NMR (400 MHz, CDCl3) δ 7.37-7.26 (m, 1H), 7.23 (dd, J=9.0, 2.8 Hz, 1H), 7.06 (m, 1H), 3.84 (s, 2H), 3.73 (s, 3H), 3.33 (s, 1H). LCMS-A: rt 5.838 min; m/z 193 [M+H]+.
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