1,10-Dibromodecane → 13-(4-Methylphenyl)tridecyl bromide

Participants

Reaction Conditions

Reaction Steps

A solution of 3-(4-methylphenyl)propylmagnesium bromide is prepared by reacting 20 g. 3-(4-methylphenyl)propyl bromide with 2.5 g. of magnesium turnings in 50 ml. dry tetrahydrofuran. The solution of Grignard reagent is added dropwise to a stirred, cold (-10° C.) solution of 30 g. of 1,10-dibromodecane and 0.2 g. of lithium tetrachlorocuprate in 75 ml. dry tetrahydrofuran at a rate such that the reaction temperature does not exceed -5° C. After one addition hour of stirring at -10° C., the solvent is evaporated and the resultant liquid is fractionated in vacuo to yield 13-(4-methylphenyl)tridecyl bromide as a colorless liquid.

Provenance & Evidence