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

Temperature

-70 °C

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 allowed to stir and warm to room temperature overnight. The solution was cooled to −70° C. and an additional 0.4 mol n-butyl lithium was added over a one-hour period. The resulting slurry was stirred for one hour at −70° C., warmed to −10° C. over a two-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. @ 0.5 mmHg.

1. additionwas added dropwise over a one-hour period
2. customnear −70° C
3. temperaturewarmed to −10° C. over a two-hour period
4. customwas then recooled to −70° C.
5. stirringto stir
6. temperaturewarm to room temperature overnight
7. temperatureThe solution was cooled to −70° C.
8. stirringThe resulting slurry was stirred for one hour at −70° C.
9. temperaturewarmed to −10° C. over a two-hour period
10. customrecooled to −70° C
11. temperatureto warm to room temperature overnight
12. customThe mixture was quenched with water
13. customthe layers were separated
14. washThe organic layer was washed twice with sodium bicarbonate solution and with salt brine
15. dry with materialthen dried over magnesium sulfate
16. customThe solvents were evaporated under vacuum
17. distillationthe product distilled twice under vacuum

ORD record

ord-9da823d4b62b45bdb197c72e0744401e

Source dataset

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06559262B1