Chloride → 11-(Trimethylsilyl)undecyl bromide

Participants

Reaction Steps

The 3-(trimethylsilyl)propyl magnesium bromide prepared from 40 g. 3-(trimethylsilyl)propyl bromide and 5.1 g. magnesium turnings in 150 ml. dry ether was dropwise added to a cole (-20°) solution of 42 g. 1,8-dibromooctane, 170 mg. lithium chloride, and 270 mg. cuprus chloride in 120 ml. dry tetrahydrofuran under an argon atmosphere. When addition of the Grignard reagent was complete, the reaction was warmed to room temperature and stirring was continued for 17 hr. The solution was treated with 200 ml. 10% hydrochloric acid, the layers were separated, and the aqueous phase was washed twice with 100 ml. portions of ether. The combined organic phases were washed with brine, dried with anhydrous magnesium sulfate, and evaporated to a colorless liquid. Distillation of the crude product yielded the title compound.

Provenance & Evidence