Sodium Azide → 2-Azido-1-(4-fluorophenyl)ethan-1-one

HRID 1985859Notes

Reaction equation

HRID 1985859 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[N-:12]=[N+:13]=[N-:14].[Na+]>CS(C)=O>[N:12]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4])=[N+:13]=[N-:14]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 967492-Bromo-1-(4-fluorophenyl)ethan-1-one

Product 1

HCID 139300882-Azido-1-(4-fluorophenyl)ethan-1-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-bromo-1-(4-fluoro-phenyl)-ethanone (1 eq) in DMSO at 10° C. is vigorously stirred and sodium azide (1.25 eq) is added. The mixture is stirred for 1 hour then quenched with water and extracted with ethyl acetate (2×). The combined organic layers are washed with water and brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure to give 2-azido-1-(4-fluoro-phenyl)-ethanone.

Workup

  1. customthen quenched with water
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4bae9cb6a4ed401b88e3b65589f3e92e
Source dataset
uspto-grants-2009_06
Patent number
US07547717B2

Reaction notes

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