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

HRID 2221067Notes

Reaction equation

HRID 2221067 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-oneYield 80.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 2-bromo-1-(4-fluoro-phenyl)-ethanone (2.5 g, 11.5 mmol) in DMSO (15 mL) at 10° C. was vigorously stirred and sodium azide (0.94 g, 14.4 mmol) was added. The mixture was stirred for I hour then quenched with water (20 mL) and extracted with ethyl acetate (2×25 mL). The combined organic layers were washed with water (25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduce pressure to give 2-azido-1-(4-fluoro-phenyl)-ethanone (1.7 g, 9.3 mmol) as a viscous yellow-red liquid.

Workup

  1. customthen quenched with water (20 mL)
  2. extractionextracted with ethyl acetate (2×25 mL)
  3. washThe combined organic layers were washed with water (25 mL) and brine (25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1d94551797d1408996415e00c99fc73b
Source dataset
uspto-grants-2008_05
Patent number
US07368467B2

Reaction notes

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