Chlorotrimethylsilane → (2,5-Dimethyl-1,4-phenylene)bis(trimethylsilane)

10.52 g of 2,5-dibromo-p-xylene (40 mmol) was reacted with 2.08 of magnesium turnings (88 mmol) in 40 ml of anhydrous THF for 4 hours with refluxing (initiated by iodine) to give the 2,5-bisbromomagnesium-p-xylene Grignard reagent. To this solution, cooled in an ice bath, was added a solution of 11.2 ml trimethylsilyl chloride (88 mmol) in 40 ml of anhydrous THF. The mixture was refluxed for 24 hours and then cooled in an ice bath. After it was quenched with saturated ammonium chloride aqueous solution, THF was evaporated and the residue was extracted with hexane (30 ml×2). The combined organic layers were washed with water, brine and then dried over anhydrous magnesium sulfate. After the solution was evaporated under a reduced pressure, the residue was recrystallized in ethanol to afford white plate crystals 6.1 g, (yield 61%). M.p. 56.0-57.5° C. MS: 250. 1H NMR (300 MHz, CDCl3, ppm) δ 0.31 (18H, s, —Si(CH3)3), 2.42 (6H, s), 7.24 (2H, s). Anal. Calcd for C14H26Si2: C, 67.12; H, 10.46. Found: C, 66.94; H, 10.23.

1. temperatureTo this solution, cooled in an ice bath
2. temperatureThe mixture was refluxed for 24 hours
3. temperaturecooled in an ice bath
4. customAfter it was quenched with saturated ammonium chloride aqueous solution, THF
5. customwas evaporated
6. extractionthe residue was extracted with hexane (30 ml×2)
7. washThe combined organic layers were washed with water, brine
8. dry with materialdried over anhydrous magnesium sulfate
9. customAfter the solution was evaporated under a reduced pressure
10. customthe residue was recrystallized in ethanol

ORD record

ord-819f043ca0b542a8897d0fb9a8cceb34

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06885038B2