Chlorotrimethylsilane → (6-Bromo-2,3-difluorophenyl)trimethylsilane

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Reaction Conditions

Reaction Steps

Diisopropylamine (2.62 g, 25.9 mmol) was added drop wise to a solution of n-BuLi (2.5 M in hexane, 10.4 mL, 26.0 mmol) in anhydrous THF (19 mL) at −78° C., then the solution was stirred at −78° C. for 15 minutes. To this solution was added 4-bromo-1,2-difluorobenzene (5.00 g, 25.9 mmol), then the mixture was stirred at −78° C. for 2 hours. Freshly distilled chlorotrimethylsilane (2.81 g, 25.9 mmol) was added, then the mixture was allowed to warm to room temperature slowly over two hours. The mixture was diluted with saturated NaCl (aq) then extracted with EtOAc (3×40 mL). The combined organic layers were dried over MgSO4, filtered, then concentrated to afford the title compound as a light yellow oil. This material was used directly in the next step without further purification. 1H NMR (500 MHz, CDCl3): δ 7.27 (ddd, J=8.7, 4.0, 1.7 Hz, 1H); 7.00 (q, J=8.9 Hz, 1H); 0.47 (s, 9H).

Provenance & Evidence