Reaction #927245

Reaction equation

1-chlorodec-4-yne

lithium bromide

Ether

1-chlorodec-4-yne

→

1-bromodec-4-yne

Solvents

THF

Conditions

Workup

1. 1
   Washthe reaction mixture was washed with water (2×) and brine
2. 2
   Dryingdried over magnesium sulfate
3. 3
   workup.DISSOLUTIONThe product was dissolved in 70 ml of THF
4. 4
   Temperaturerefluxed for 8 hours with an additional 25 g of lithium bromide

Procedure

1-Bromodec-4-yne was prepared from 1-chlorodec-4-yne. The 1-chlorodec-4-yne (10.6 g, 61 mmol) and 25 g of lithium bromide were refluxed in 80 ml of THF for 21 hours. The conversion was 74%. Ether was added, the reaction mixture was washed with water (2×) and brine, dried over magnesium sulfate and stripped. The product was dissolved in 70 ml of THF and refluxed for 8 hours with an additional 25 g of lithium bromide. This gave 95% conversion of the chloride to the bromide. The same workup provided 11.36 g of 1-bromodec-4-yne.

Source