Benzyl Bromide → Benzyl azide

HRID 478959Notes

Reaction equation

HRID 478959 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5](Br)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CS(C)=O>[CH2:5]([N:1]=[N+:2]=[N-:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 33557Sodium Azide

Product 1

HCID 12152Benzyl azideYield 99%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of sodium azide (76 g, 1.169 mol), dimethylsulfoxide (800 ml) and benzyl bromide (100 g, 0.584 mol) is stirred at room temperature for 5 hours. The reaction mixture is then slowly poured into ice water and extracted with ether (3×400 ml). The combined organic extracts are washed with water (500 ml), brine (500 ml) and dried over sodium sulfate. Removal of the volatiles in vacuo affords pure title compound (77 g, 99%) as a colorless oil.

Workup

  1. extractionextracted with ether (3×400 ml)
  2. washThe combined organic extracts are washed with water (500 ml), brine (500 ml)
  3. dry with materialdried over sodium sulfate
  4. customRemoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-0004fc97a9904d4ba943a20d2d88a11b
Source dataset
uspto-grants-2003_11
Patent number
US06642390B2

Reaction notes

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