Reaction #927259

Reaction equation

hydrochloric acid

bromoform

2-pentyl-hept-1-ene

potassium t-butoxide

→

2,2-dibromo-1,1-dipentyl-cyclopropane

Yield 83.4%

Solvents

water

—

pentanes

Conditions

Workup

1. 1
   workup.ADDITIONwas added slowly via addition funnel
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 a solution of 4.16 g (0.0247 mol) of 2-pentyl-hept-1-ene in 31 ml of pentanes, was added 4.95 g (0.0441 mol) of potassium t-butoxide. While cooling the resulting mixture to an internal temperature of 5° C., 4.01 ml ( 0.0459 mol) of bromoform was added slowly via addition funnel. The reaction mixture was allowed to warm naturally to room temperature and left overnight. To the reaction mixture was added 25 ml of water then 36 ml of 1 N hydrochloric acid. 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 7.00 g (83.4% of theory) of 2,2-dibromo-1,1-dipentyl-cyclopropane as an oil.

Source