Sodium Azide → (2-Azido-1,1-difluoroethyl)benzene

HRID 911570Notes

Reaction equation

HRID 911570 reaction equation
FC(F)(F)S(O[CH2:7][C:8]([F:16])([F:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C.O>[N:19]([CH2:7][C:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([F:16])[F:15])=[N+:20]=[N-:21]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 22138897HCID 22138897, compound

Product 1

HCID 57656188(2-Azido-1,1-difluoroethyl)benzeneYield 99.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Heat at 60° C. a solution of 2,2-difluoro-2-phenyl-ethyl trifluoromethanesulfonate (759 mg, 2.617 mmol) and sodium azide (357 mg, 5.496 mmol) in anhydrous DMF (10 mL) under nitrogen for 3 h. Cool the reaction mixture to room temperature. Dilute with water and extract the aqueous phase twice with diethyl ether. Wash the combined organic extracts twice with ice-cold water, dry over Na2SO4, filter and concentrate in vacuo to provide the desired intermediate as an oil (475 mg, 99%) that was used without any further purification.

Workup

  1. extractionextract the aqueous phase twice with diethyl ether
  2. washWash the combined organic extracts twice with ice-cold water
  3. dry with materialdry over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-bc8b4ec63abf4b87bb3f9d48b6653295
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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