Reaction #927242

Reaction equation

2-bromo-oct-1-ene

bromoform

N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium dibromide

potassium hydroxide

→

1,1,2-tribromo-2-hexyl-cyclopropane

Yield 51.0%

Solvents

methylene chloride

—

hexanes

water

Conditions

Workup

1. 1
   Filtrationfiltered through qualitative fluted filter paper
2. 2
   OtherThe resulting mixture was transferred to a separatory funnel
3. 3
   Otherthe phases were separated
4. 4
   DryingThe organic layer was dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   OtherThe solvent was removed from the filtrate in vacuo

Procedure

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.

Source