Bromoform → 1,1,2-Tribromo-2-hexyl-cyclopropane

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Reaction Steps

To 5.42 g (0.0284 mol) of 2-bromo-oct-1-ene in 7.42 ml (0.0851 mol) of bromoform and 48.8 ml of methylene chloride, were added 1.30 g ( 0.00284 mol) of N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide and 12.1 ml (0.142 mol) of 45% aqueous potassium hydroxide. The mixture was left at room temperature for 5 days. There was then added hexanes and water. This mixture was gravity filtered through qualitative fluted filter paper. The resulting mixture was transferred to a separatory funnel and the phases were separated. The organic layer was dried over MgSO4 and filtered. The solvent was removed from the filtrate in vacuo to yield 5.25 g (51.0% of theoretical) of 1,1,2-tribromo-2-hexyl-cyclopropane as an oil.

Provenance & Evidence