Chlorotrimethylsilane → (5-Bromo-1,3-phenylene)bis(trimethylsilane)

Participants

Reaction Conditions

Reaction Steps

1,3,5-Tribromobenzene (125 g, 0.4 mol) was dissolved in anhydrous diethylether (1 L), and cooled to −70° C. n-butyllithium (250 mL. 1.6 M in hexanes. 0.4 mol) was added dropwise over a one-hour period keeping the temperature near −70° C. The solution was stirred for an additional 20 minutes at −70° C. and then warmed to −10° C. over a two-hour period. The solution was then recooled to −70° C. and trimethylchlorosilane (45 g, 0.4 mol) was added over a one-hour period. The solution was stirred and allowed to warm to room temperature overnight. The solution was cooled to −70° C. and an additional 0.4 mol n-butyllithium was added over a one-hour period. The resulting slurry was stirred for one hour at −70° C., warmed to −10° C. over a one-hour period and then recooled to −70° C. An additional 0.4 mol of trimethylchlorosilane was added and the slurry was allowed to warm to room temperature overnight. The mixture was quenched with water and the layers were separated. The organic layer was washed twice with sodium bicarbonate solution and with salt brine then dried over magnesium sulfate. The solvents were evaporated under vacuum and the product distilled twice under vacuum to yield 85.2 g (70%) of a colorless liquid. b.p. 100-105° C. at 0.5 mmHg.

Provenance & Evidence