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

HRID 2264094Notes

Reaction equation

HRID 2264094 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-b1398e5856d54be2b113f82bc8eef2e5
Source dataset
uspto-grants-2010_12
Patent number
US07850947B2

Reaction notes

Loading…