Sodium Azide → 4-Azidomethyl-2,5-difluorobenzonitrile

HRID 1990766Notes

Reaction equation

HRID 1990766 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[C:11]([F:13])[C:10]([C:14]#[N:15])=[CH:9][C:8]=1[F:16])(=O)=O.[N-:17]=[N+:18]=[N-:19].[Na+]>O.CN(C=O)C>[N:17]([CH2:6][C:7]1[C:8]([F:16])=[CH:9][C:10]([C:14]#[N:15])=[C:11]([F:13])[CH:12]=1)=[N+:18]=[N-:19]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 219046244-Cyano-2,5-difluorobenzyl methanesulfonate

Product 1

HCID 219046104-Azidomethyl-2,5-difluorobenzonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-cyano-2,5-difluorobenzyl methanesulfonate (4.5 g, 0.0182 mol; see step (iv) above) and sodium azide (2.0 g, 0.031 mol) in 20 mL of water and 40 mL of DMF was stirred at room temperature for 2 h. It was subsequently poured into 300 mL of water and extracted three times with diethyl ether. The combined ethereal phase was washed several times with water, dried (Na2SO4) and evaporated. A small sample was evaporated for NMR purposes and the product crystallised. The rest was evaporated cautiously but not until complete dryness. Yield (theoretically 3.5 g) is assumed to be almost quantitative based on NMR and analytical HPLC.

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined ethereal phase was washed several times with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customA small sample was evaporated for NMR purposes
  6. customthe product crystallised
  7. customThe rest was evaporated cautiously but not until complete dryness
  8. customYield (theoretically 3.5 g)

Sources & evidence

ORD record
ord-e05a48e62e7b49eeb6177f3dd9a41440
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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