Reaction #927241

Reaction equation

diethylether

2,3-dibromopropene

pentylmagnesium bromide

diethyl ether

hydrochloric acid

→

2-bromo-oct-1-ene

Conditions

Workup

1. 1
   TemperatureWhile cooling in an ice water bath
2. 2
   Temperaturecooling in an ice water bath
3. 3
   OtherThe resulting mixture was transferred to a separatory funnel
4. 4
   Otherthe phases were separated
5. 5
   DryingThe organic layer was dried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   OtherThe solvent was removed from the filtrate in vacuo

Procedure

A solution of 9.42 ml (0.0728 mol) of 2,3-dibromopropene in 70 ml diethylether was placed under a nitrogen atmosphere by use of a Firestone valve. While cooling in an ice water bath, a solution of 0.091 mol of pentylmagnesium bromide in 70 ml diethyl ether was added slowly via addition funnel. After stirring for 2 hours while warming to room temperature, there was then added via syringe 50 ml of 1 N hydrochloric acid to the reaction cooling in an ice water bath. 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 15.0 g (85.7% of theory) of 81% pure 2-bromo-oct-1-ene as an oil.

Source