Sodium Azide → 1-(azidomethyl)-4-chlorobenzene

HRID 1663351Notes

Reaction equation

HRID 1663351 reaction equation
[Cl: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+]>CC(C)=O>[N:10]([CH2:6][C:5]1[CH:8]=[CH:9][C:2]([Cl:1])=[CH:3][CH:4]=1)=[N+:11]=[N-:12]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 693291-(Bromomethyl)-4-chlorobenzene

Product 1

HCID 111711941-(azidomethyl)-4-chlorobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 4-chlorobenzyl bromide in acetone was treated with NaN3 and refluxed for 3 hours. The reactions was concentrated by 50% and diluted with saturated sodium chloride solution. The reaction was then extracted with Et2O, washed with brine, dried (Na2SO4) and concentrated to give 1-(azidomethyl)-4-chlorobenzene.

Workup

  1. temperaturerefluxed for 3 hours
  2. concentrationThe reactions was concentrated by 50%
  3. additiondiluted with saturated sodium chloride solution
  4. extractionThe reaction was then extracted with Et2O
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-27e03a3737b945459e1f7dc864b160e4
Source dataset
uspto-grants-2011_10
Patent number
US08034943B2

Reaction notes

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