Sodium Hydroxide → 3-Bromo-2-ethynyl-5-(trifluoromethyl)benzenamine

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Sodium hydroxide (3.17 mL, 31.7 mmol) was added to a solution of 3-bromo-5-(trifluoromethyl)-2-((trimethylsilyl)ethynyl)aniline (10.67 g, 31.7 mmol) in methanol (200 mL) and was stirred for 30 min. The solvent was evaporated. The residue was taken up in brine (30 mL) and extracted with ethyl acetate (3×100 mL). The combined organic layers were dried with magnesium sulfate and evaporated. The residue was purified on silica gel with 10% ethyl acetate/hexanes to give 7.54 g (90%) as a tan solid. 1H-NMR (CDCl3, 400 MHz) δ 7.15 (s, 1H), 6.85 (s, 1H), 4.58 (bs, 2H), 3.77 (s, 1H); LC/MS (HPLC method 4): tR=3.186 min, 263.89(MH)+.

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