Water → Methyl 2-(azidomethyl)-3-nitrobenzoate

HRID 1869303Notes

Reaction equation

HRID 1869303 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13]Br.CN(C)C=O.O.[N-:22]=[N+:23]=[N-:24].[Na+]>COC(C)(C)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][N:22]=[N+:23]=[N-:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 33557Sodium AzideHCID 1487795Methyl 2-(bromomethyl)-3-nitrobenzoate

Product 1

HCID 71417999Methyl 2-(azidomethyl)-3-nitrobenzoateYield 89.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

10 g (36.5 mmol) of 2-(bromomethyl)-3-nitrobenzoic acid methyl ester is mixed with 36 ml of N,N-dimethylformamide and 24 ml of water. After 3.54 g of sodium azide is added, the batch is stirred overnight. The reaction mixture is diluted with methyl-tert butyl ether, and washed twice with water and once with brine. After drying on sodium sulfate, it is filtered, and the solvent is spun off. The desired azide is obtained in a yield of 89.6% (7.72 g) and further incorporated in crude form.

Workup

  1. washwashed twice with water and once with brine
  2. customAfter drying on sodium sulfate, it
  3. filtrationis filtered

Sources & evidence

ORD record
ord-8743ec3abc56406cbf30b052dce8e164
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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