4-Bromo-2,6-xylidine → N-(4-Bromo-2,6-dimethylphenyl)(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silanamine

Participants

Reaction Steps

Under an argon atmosphere, to a solution of 11.2 g (55.9 mmol) of 4-bromo-2,6-dimethylaniline in 170 ml of THF, 22.4 ml of 2.5 M (55.9 mmol) nBuLi in hexanes were added at −80° C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 12.0 g (55.9 mmol) of chloro(dimethyl)(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane in 80 ml of THF. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue 100 ml of toluene were added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 170-175° C./0.6 mm Hg. The product crystallizes slowly at ambient temperature. Yield 8.45 g (40%).

Provenance & Evidence