Sodium Azide → 4-Azidomethyl-2-fluorobenzonitrile

HRID 1717492Notes

Reaction equation

HRID 1717492 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1)(=O)=O.[N-:16]=[N+:17]=[N-:18].[Na+]>O>[N:16]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[C:9]([F:15])[CH:8]=1)=[N+:17]=[N-:18]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 219046204-Cyano-3-fluorobenzyl methanesulfonate

Product 1

HCID 219046434-Azidomethyl-2-fluorobenzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cooled solution of 4-cyano-3-fluorobenzyl methanesulfonate (1.8 g, 7.9 mmol; see step (iii) above) was added sodium azide (0.80 g, 0.012 mol). The mixture was stirred overnight and then poured into 200 mL of water and extracted three times with diethyl ether. The combined ethereal phase washed five times with water, dried (Na2SO4) and evaporated. The crude colourless oil could be used without further purification. Yield: 1.2 g (87%).

Workup

  1. extractionextracted three times with diethyl ether
  2. washThe combined ethereal phase washed five times with water
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude colourless oil could be used without further purification

Sources & evidence

ORD record
ord-d91c0f3eeefe4e2db5924a5ebac5a6d2
Source dataset
uspto-grants-2010_09
Patent number
US07803954B2

Reaction notes

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