Sodium Azide → 4-Bromobenzyl azide

HRID 511991Notes

Reaction equation

HRID 511991 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6]Br)=[CH:4][CH:3]=1.[N-:10]=[N+:11]=[N-:12].[Na+]>CN(C=O)C.O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:10]=[N+:11]=[N-:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 685274-Bromobenzyl bromide

Product 1

HCID 109875654-Bromobenzyl azideYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-bromobenzyl bromide (54) and sodium azide (2.0 equiv.) in DMF was stirred at 50° C. for 3 h. The reaction mixture was diluted with water and extracted with CH2Cl2. The combined organic extract was dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chromatography to yield 55 as colorless oil in 92% yield.

Workup

  1. extractionextracted with CH2Cl2
  2. extractionThe combined organic extract
  3. dry with materialwas dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-be285720f74844ac9e2e1175a5d03926
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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