Azidotrimethylsilane → 1-(2-Azido-2-methylpropyl)-4-(trifluoromethyl)benzene

HRID 244953Notes

Reaction equation

HRID 244953 reaction equation
[CH3:1][C:2](O)([CH3:14])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1.C[Si]([N:20]=[N+:21]=[N-:22])(C)C>C(Cl)Cl>[N:20]([C:2]([CH3:14])([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1)=[N+:21]=[N-:22]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 651450142-Methyl-1-(4-(trifluoromethyl)phenyl)propan-2-ol

Product 1

HCID 866974731-(2-Azido-2-methylpropyl)-4-(trifluoromethyl)benzeneYield 86.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

26.3 g of 2-methyl-1-(4-(trifluoromethyl)phenyl)propan-2-ol was dissolved in 400 mL of methylene chloride, and 25 mL (0.19 mol) of trimethylsilyl azide and 24 mL (0.19 mol) of boron trifluoride diethyl ether complex were added dropwise under cooling with ice. The reaction mixture was stirred at room temperature for 20 hours. After completion of the reaction, the reaction mixture was washed with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively, dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 25.4 g of the desired product.

Workup

  1. temperatureunder cooling with ice
  2. customAfter completion of the reaction
  3. washthe reaction mixture was washed with saturated aqueous sodium hydrogen carbonate and with saturated aqueous sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-7c0bfcfffe2043caa376f8bc7bfa3f62
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

Loading…