Sodium Azide → 2,2,2-Trifluoro-1-phenylethyl azide

HRID 650099Notes

Reaction equation

HRID 650099 reaction equation
[F:1][C:2]([F:16])([F:15])[CH:3](CS([O-])(=O)=O)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N-:17]=[N+:18]=[N-:19].[Na+]>CN(C=O)C>[F:1][C:2]([F:16])([F:15])[CH:3]([N:17]=[N+:18]=[N-:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 131722828alpha-(Trifluoromethyl)benzylmesylate

Product 1

HCID 5553562,2,2-Trifluoro-1-phenylethyl azideYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of α-(trifluoromethyl)benzylmesylate (2.8 g, 11.0 mmol) in DMF (15 mL), sodium azide (7.38 g, 110 mmol) was added. The reaction mixture was stirred at 60° C. for 48 hours. Then the reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel gave the desired product (849 mg, 37%). EI-MS m/z 202 (M+).

Workup

  1. customThen the reaction mixture was partitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1901c5ca357948adbf01d262f3c145ee
Source dataset
uspto-grants-2001_08
Patent number
US06271261B1

Reaction notes

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