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With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20.0℃; for 0.166667h;
A mixture of bis (benzonitril) dichloropalladium (II) (53 mg, 0.14 mmol) and copper (I) iodide (26 mg, 0.14 mmol) in 6 mL dry THF was purged with argon for 3 minutes, then was added tri (tert-butyl phosphine) (69 ul, 0.28 mmol), TMS acetylene (0.77 ml, 5.5 mmol), 3-bromo-4-fluoronitrobenzene 505 mg, 2.295 mmol), and di-isopropylamine (0.77 ml, 5.5 mmol). The mixture was stirred at room temperature for 5 hours under argon. To the reaction mixture was added 7 mL 1 M TBAF/THF and the mixture was stirred at room temperature for 10 minutes. Workup and purification by column chromatography (silica, 5% - 35% EtOAc/hexane) give 2-ethynyl-1-fluoro-4-nitro-benzene.
With hydrogen;5% Pd-BaSO4; In ethanol; under 760.051 Torr; for 1.5h;
To a solution of <strong>[343866-99-9]2-ethynyl-1-fluoro-4-nitro-benzene</strong> (70 mg, 0.42 mmol, obtained in Example 71) in 3 mL ethanol, 5% Pd/BaS04 (48 mg) was added. The mixture was hydrogenated at 1 atm for 1.5 hrs. Catalyst was removed by filtering through a celite pad. The filtrate was concentrated to give pure 1-fluoro-4-nitro-2-vinyl-benzene.
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