Sodium Azide → Methyl 4-(azidomethyl)-2-chlorobenzoate

HRID 2355272Notes

Reaction equation

HRID 2355272 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14]Br)=[CH:10][C:9]=1[Cl:16]>CN(C)C=O>[CH3:5][O:6][C:7](=[O:17])[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][N:1]=[N+:2]=[N-:3])=[CH:10][C:9]=1[Cl:16]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 22072833Methyl 4-(bromomethyl)-2-chlorobenzoate

Product 1

HCID 57461226Methyl 4-(azidomethyl)-2-chlorobenzoateYield 89.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Add sodium azide (2.44 g, 37.49 mmol) to crude 4-bromomethyl-2-chloro-benzoic acid methyl ester (7.6 g, 28.84 mmol) in anhydrous dimethylformamide (100 mL) at room temperature under argon gas. Stir the reaction mixture at 50° C. overnight. Quench the reaction mixture with water and extract with ether (3×). Combine the organic layers, wash with brine, dry over sodium sulfate, and concentrate to provide the crude product (5.8 g, 25.7 mmol).

Workup

  1. customQuench the reaction mixture with water
  2. extractionextract with ether (3×)
  3. washCombine the organic layers, wash with brine
  4. dry with materialdry over sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-30dd83ab2ae8426a8bc1992b23881f86
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

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