Chlorotrimethylsilane → (3-Chlorothiophen-2-yl)trimethylsilane

Participants

Reaction Conditions

Reaction Steps

To 3-chlorothiophene (5.0 g, 42.16 mmol), dissolved in 50 mL of tetrahydrofuran stirring at -72° C. (acetone/dry ice bath), was added 16.8 ml of 2.5M hexane solution of n-butyllithium over a 15 minute period. The reaction temperature was maintained below -70° C. during the addition. Soon after complete addition of the n-butyllithium a white precipitate formed. After 40 minutes of stirring below -70° C., 5.88 mL of chlorotrimethylsilane was slowly added over a 5 minute period. After addition the solution momentarily became clear before turning cloudy again by the formation of lithium chloride by-product. After 10 minutes the reaction solution was warmed to 0° C. At 0° C. 5 mL of water followed by 25 mL of brine was added to quench the reaction. The aqueous solution was then extracted with ethyl acetate (2×30 mL). The organic extract was dried (Na2SO4), filtered and evaporated to 8.0 g of title compound as a clear oil.

Provenance & Evidence