Dimethylformamide → 2-(Azidomethyl)-5-fluoro-3-nitrobenzoic Acid Methyl Ester

HRID 1869322Notes

Reaction equation

HRID 1869322 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[CH2:14]Br.CN(C)C=O.[N-:22]=[N+:23]=[N-:24].[Na+]>O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[C:6]([N+:11]([O-:13])=[O:12])[C:5]=1[CH2:14][N:22]=[N+:23]=[N-:24]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 68679319Methyl 2-(bromomethyl)-5-fluoro-3-nitrobenzoate

Product 1

HCID 860442842-(Azidomethyl)-5-fluoro-3-nitrobenzoic Acid Methyl EsterYield 95.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.47 g (8.46 mmol) of 2-(bromomethyl)-5-fluoro-3-nitrobenzoic acid methyl ester is mixed with 8.3 ml of N,N-dimethylformamide and 5.5 ml of water. After 0.82 g (12.66 mmol) of sodium azide is added, the batch is stirred overnight. The reaction mixture is added to water and extracted three times with methyl tert-butyl ether. The combined organic extracts are washed with water and with brine. After drying on sodium sulfate, it is filtered, and the solvent is spun off. Chromatography on a Flashmaster yields 2.06 g (95.8%) of the desired azide.

Workup

  1. extractionextracted three times with methyl tert-butyl ether
  2. washThe combined organic extracts are washed with water and with brine
  3. customAfter drying on sodium sulfate, it
  4. filtrationis filtered

Sources & evidence

ORD record
ord-02fc3780f3cb472cb7340bbc5b29d93a
Source dataset
uspto-grants-2009_12
Patent number
US07638515B2

Reaction notes

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