Water → 1-(Azidomethyl)-2-bromobenzene

HRID 1736617Notes

Reaction equation

HRID 1736617 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Br:9].[N-:10]=[N+:11]=[N-:12].[Na+].O>CN(C)C=O>[N:10]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Br:9])=[N+:11]=[N-:12]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 769652-Bromobenzyl bromide

Product 1

HCID 146120561-(Azidomethyl)-2-bromobenzeneYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

After a mixture of 30 g (120 mmol) of 1-bromomethyl-2-bromobenzene and 15.6 g (240 mmol) of sodium azide in 300 ml of dimethylformamide was stirred at 25° C. for 20 hours it was poured into 500 ml of water and extracted with ethyl acetate. The extracts were washed with water and brine, dried (Na2SO4) and concentrated to give 24.9 g (98%) of the product as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2681c09ddf8548d79744985e717bb86b
Source dataset
uspto-grants-1996_07
Patent number
US05541286

Reaction notes

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