Sodium Azide → 1-[3,5-Bis(trifluoromethyl)phenyl]ethyl azide

HRID 1399514Notes

Reaction equation

HRID 1399514 reaction equation
Br[C@@H:2]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([C:14]([F:17])([F:16])[F:15])[CH:5]=1)[CH3:3].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C)C=O>[F:15][C:14]([F:17])([F:16])[C:6]1[CH:5]=[C:4]([CH:2]([N:18]=[N+:19]=[N-:20])[CH3:3])[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=1

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 56643876(R)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane

Product 1

HCID 727612691-[3,5-Bis(trifluoromethyl)phenyl]ethyl azideYield 117.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-16.5 °C

Procedure

A solution of (R)-1-bromo-1-[3,5-bis(trifluoromethyl)phenyl]ethane (2) (106 mg, 0.336 mmol, 99% ee) obtained in 1-(a) mentioned above in N,N-dimethylformamide (1 mL) was added with sodium azide (64.4 mg, 0.990 mmol), and the mixture was stirred at −18 to −15° C. for 4 hours. The reaction solution was extracted with ethyl acetate/n-hexane (1:1) and water, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure to obtain 111.5 mg of 1-[3,5-bis(trifluoromethyl)phenyl]ethyl azide (crude product: 111.5 mg).

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate/n-hexane (1:1) and water
  2. washthe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2029cff88ee140388f3a157e926b1bb0
Source dataset
uspto-grants-2014_12
Patent number
US08906895B2

Reaction notes

Loading…