Benzyl Bromide → Benzyl azide

HRID 1728353Notes

Reaction equation

HRID 1728353 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:9]=[N+:10]=[N-:11].[Na+]>C(O)C>[CH2:1]([N:9]=[N+:10]=[N-:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 33557Sodium Azide

Product 1

HCID 12152Benzyl azideYield 60.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 24 mL (0.2 mol) of benzyl bromide dissolved in 42 mL of absolute ethanol was added 14.3 g (0.22 mol) of sodium azide. The mixture was refluxed slowly for 3 hours, cooled to ambient temperature and filtered. The filtrate was concentrated in vacuo and the resulting residue was diluted with 800 mL of heptane. Insoluble material was removed by filtration and the filtrate concentrated under reduced pressure to give 16.0 g (60%) of benzyl azide which was used without further purification.

Workup

  1. temperatureThe mixture was refluxed slowly for 3 hours
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe resulting residue was diluted with 800 mL of heptane
  5. customInsoluble material was removed by filtration
  6. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-300b4d542d084b3b862e52b107941c20
Source dataset
uspto-grants-1994_07
Patent number
US05326776

Reaction notes

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