Benzyl Bromide → Benzyl azide

HRID 1893453Notes

Reaction equation

HRID 1893453 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+]>CN(C)C=O.C(OCC)(=O)C>[N:9]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[N+:10]=[N-:11]

Participants

5

Reactant 2

HCID 7498Benzyl BromideHCID 33557Sodium Azide

Product 1

HCID 12152Benzyl azideYield 80%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzylbromide (350 μL, 2.92 mmol) in anhydrous dimethylformamide (7 mL), under argon, was added sodium azide (288 mg, 6.43 mmol). After 24 h at room temperature, the reaction mixture was diluted with ethyl acetate and then washed three times with brine. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The residue was diluted with water and extracted with pentane, dried over sodium sulfate, filtered and evaporated to afford the title compound (309 mg, 80%) as a colorless oil.

Workup

  1. washwashed three times with brine
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. additionThe residue was diluted with water
  6. extractionextracted with pentane
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-992498611aa84445817e6465f9104c9c
Source dataset
uspto-grants-2013_08
Patent number
US08513250B2

Reaction notes

Loading…