Sodium Azide → 1-(Azidomethyl)-4-(trifluoromethyl)benzene

HRID 240769Notes

Reaction equation

HRID 240769 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]([F:16])([F:15])[C:7]1[CH:14]=[CH:13][C:10]([CH2:11]Br)=[CH:9][CH:8]=1>CS(C)=O.C(OCC)(=O)C>[N:1]([CH2:11][C:10]1[CH:9]=[CH:8][C:7]([C:6]([F:5])([F:15])[F:16])=[CH:14][CH:13]=1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzene

Product 1

HCID 498459471-(Azidomethyl)-4-(trifluoromethyl)benzene

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium azide (2.30 g, 35.4 mmol) was added to a solution of 4-(trifluoromethyl)benzyl bromide (4.26 g, 17.8 mmol) dissolved in dimethyl sulfoxide (15 mL) and stirred at ambient temperature overnight. The mixture was diluted with ethyl acetate, washed with water and brine, and dried over sodium sulfate. After filtration, the solvent was removed under reduced pressure to afford the title compound. The crude product was used in the next step without further characterization.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c0041892b7b94bc08fcecf4a0763adef
Source dataset
uspto-grants-2014_02
Patent number
US08648069B2

Reaction notes

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