Sodium Azide → Methyl 4-(azidomethyl)-3-methoxybenzoate

HRID 1434484Notes

Reaction equation

HRID 1434484 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]Br)=[C:6]([O:12][CH3:13])[CH:5]=1.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:15]=[N+:16]=[N-:17])=[C:6]([O:12][CH3:13])[CH:5]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 57445596Methyl 4-(azidomethyl)-3-methoxybenzoateYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(bromomethyl)-3-methoxybenzoic acid methyl ester (8 g; 31 mmol) and NaN3 (2 g; 31 mmol) in DMF (90 mL) was stirred overnight at room temperature. The volatiles were removed under vacuum and the crude product was dissolved in EtOAc (50 mL). The solution was washed with water (2×50 mL) and dried. The volatiles were evaporated to provide 4-(azidomethyl)-3-methoxybenzoic acid methyl ester (6.68 g; 30 mmol). Yield 97%.

Workup

  1. customThe volatiles were removed under vacuum
  2. dissolutionthe crude product was dissolved in EtOAc (50 mL)
  3. washThe solution was washed with water (2×50 mL)
  4. customdried
  5. customThe volatiles were evaporated

Sources & evidence

ORD record
ord-066e0ce618b444e88c4747c56c0ecd86
Source dataset
uspto-grants-2009_11
Patent number
US07611692B2

Reaction notes

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