Reaction #927247

Reaction equation

magnesium

1,2-dibromoethane

1-(1-Ethoxyethoxy)-6-bromohexane

1,2-dibromoprop-2-ene

→

yellow liquid

9-(1-Ethoxyethoxy)-2-bromonon-1-ene

Solvents

THF

THF

Conditions

Workup

1. 1
   workup.ADDITIONAt the end of the addition the reaction mixture
2. 2
   workup.STIRRINGstirred at room temperature for 15 minutes
3. 3
   Otherquenched with water
4. 4
   OtherThe reaction mixture was transferred into a separatory funnel
5. 5
   workup.ADDITIONA small amount of 1 N HCl was added
6. 6
   Otherthe phases were separated
7. 7
   Washthe ether phase was washed with water and brine
8. 8
   Dryingdried over magnesium sulfate
9. 9
   Filtrationfiltered

Procedure

A slurry of 5.6 g of magnesium turnings (230 mmol) in 100 ml of THF was treated with a small amount of 1,2-dibromoethane. 1-(1-Ethoxyethoxy)-6-bromohexane (38.5 g, 152 mmol) was fed slowly to the reaction mixture, maintaining the temperature at 40-50° C. At the end of the addition the reaction mixture was held 20 minutes, then transferred by cannula to solution of 33.4 9 (167 mmol) of 1,2-dibromoprop-2-ene in 25 ml of THF at 0C. The reaction mixture was stirred at 0° C. for 15 minutes, then stirred at room temperature for 15 minutes, then quenched with water. The reaction mixture was transferred into a separatory funnel. A small amount of 1 N HCl was added, the phases were separated, the ether phase was washed with water and brine, then dried over magnesium sulfate, filtered, and stripped to give 33.63 g of a yellow liquid which was used without further purification.

Source