Reaction #951

Reaction equation

sodium azide

4-cyanobenzyl bromide

→

4-cyanobenzyl azide

Solvents

water

DMF

toluene

Conditions

Workup

1. 1
   OtherAn exothermic reaction
2. 2
   Otherseparation of potentially explosive azide compounds it
3. 3
   workup.ADDITIONto add the toluene to the reaction mixture
4. 4
   workup.ADDITIONbefore addition of the water) and 500 ml water
5. 5
   ExtractionThe aqueous phase was extracted with an additional 2×50 ml toluene
6. 6
   WashThe combined organic extracts were washed with 2×50 ml water and brine
7. 7
   Dryingfinally dried (MgSO4)
8. 8
   Filtrationfiltered

Procedure

A solution of 20.23 g (0.31 mol) sodium azide in 50 ml water was added to 49.15 g (251 mmol) 4-cyanobenzyl bromide in 200 ml DMF at ambient temperature. An exothermic reaction took place and after 1.5 h the reaction mixture was diluted with 200 ml toluene(caution: In order to avoid separation of potentially explosive azide compounds it is adviceable to add the toluene to the reaction mixture before addition of the water) and 500 ml water. The aqueous phase was extracted with an additional 2×50 ml toluene. The combined organic extracts were washed with 2×50 ml water and brine and finally dried (MgSO4) and filtered. The solution was used as such in the next step.

Source