Sodium Azide → 2-Azido-1-(3-(trifluoromethoxy)phenyl)ethanone

HRID 419695Notes

Reaction equation

HRID 419695 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]([F:19])([F:18])[O:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](=[O:14])[CH2:12]Br>CO>[N:1]([CH2:12][C:11]([C:10]1[CH:15]=[CH:16][CH:17]=[C:8]([O:7][C:6]([F:5])([F:18])[F:19])[CH:9]=1)=[O:14])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 27786872-Bromo-3'-trifluoromethoxyacetophenone

Product 1

HCID 866320132-Azido-1-(3-(trifluoromethoxy)phenyl)ethanoneYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium azide (583 mg, 8.96 mmol) to a solution of 3-(trifluoromethoxy)-phenacyl bromide (2.17 g, 7.66 mmol) in methanol (20 mL). Stir at room temperature for 2 h. Concentrate the mixture in vacuo. Dissolve the residue in EtOAc (20 mL) and wash with water (10 mL). Dry the organic layer (Na2SO4), filter, and concentrate filtrate in vacuo to provide 2-azido-1-(3-(trifluoromethoxy)phenyl)ethanone (1.70 g, 91%). 1H-NMR (CDCl3): δ7.83 (m, 1H), 7.77 (s, 1H), 7.56 (m, 1H), 7.49 (m, 1H), 4.55 (s, 2H).

Workup

  1. concentrationConcentrate the mixture in vacuo
  2. dissolutionDissolve the residue in EtOAc (20 mL)
  3. washwash with water (10 mL)
  4. dry with materialDry the organic layer (Na2SO4)
  5. filtrationfilter
  6. concentrationconcentrate filtrate in vacuo

Sources & evidence

ORD record
ord-1b0490bc144345f1bf0475e7eaa6ff82
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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