t-Butyl bromide → 13,13-Dimethyltetradecyl bromide

Participants

Reaction Conditions

Reaction Steps

A solution of t-butylmagnesium bromide is prepared by reacting 13.7 g. of t-butyl bromide with 2.67 g. of magnesium turnings in 50 ml. dry tetrahydrofuran. The solution of Grignard reagent is dropwise added to a stirred, cold (-10° C.) solution of 36.1 g. of 1,12-dibromododecane and 0.2 g. of Li2CuCl4 in 75 ml. dry tetrahydrofuran at a rate such that the reaction temperature does not exceed -5° C. After one additional hour of stirring at -10° C., the solvent is evaporated and the resultant liquid is fractionated in vacuo to yield 13,13-dimethyltetradecyl bromide as a colorless liquid.

Provenance & Evidence