Diisopropylamine → 1-Bromo-4-(4-bromophenyl)-3-(4-methoxyphenyl)butan-2-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Diisopropylamine (0.084 g, 0.83 mmol) was dissolved in anhydrous diethyl ether (7.5 mL) under argon atmosphere and cooled to −78° C. BuLi (0.52 mL, 0.83 mmol) was added dropwise to the solution and the resulting solution was allowed to warm to 0° C. for 10 min, then recooled to −78° C. TMS-Cl (freshly distilled over calcium hydride, 0.11 mL, 0.83 mmol) was added dropwise to the solution at −78° C., after addition, the reaction was allowed to stir for an additional 10 min. The solution was then cooled to −90° C., and 4-(4-bromophenyl)-3-(4-methoxyphenyl)butan-2-one (0.25 g, 0.75 mmol) was added dropwise as a solution in anhydrous diethyl ether. After addition was complete, the solution was allowed to stir for an additional 40 min. The reaction was then warmed to 0° C. and phenyltrimethylammonium tribromide (0.31 mg, 0.83 mmol) was slowly added dropwise as a solution in anhydrous THF (4 mL). The resulting solution was allowed to stir at 25° C. for 1 hour. The mixture was diluted with EtOAc and water, washed with NaCl (×3), dried over sodium sulfate and concentrated in vacuo. The crude product was purified using silica gel chromatography (0-30% EtOAc in hexanes gradient) to afford 256 mg of 1-bromo-4-(4-bromophenyl)-3-(4-methoxyphenyl)butan-2-one as a viscous oil.

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