Sodium Azide → Methyl 4-azido-2,3,5,6-tetrafluorobenzoate

HRID 1190785Notes

Reaction equation

HRID 1190785 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:16])[C:9]([F:17])=[C:8](F)[C:7]=1[F:19]>CC(C)=O.O>[N:1]([C:8]1[C:7]([F:19])=[C:6]([F:5])[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([F:16])[C:9]=1[F:17])=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 606853Methyl Pentafluorobenzoate

Product 1

HCID 129750Methyl 4-azido-2,3,5,6-tetrafluorobenzoateYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

A mixture of NaN3 (0.6 g, 9.22 mmol) and methyl pentafluorobenzoate (1.76 g, 7.78 mmol) in acetone (16 mL) and water (6 mL) was refluxed for 8 hours. The mixture was cooled and then water (20 mL) was added, and the solution was extracted using diethyl ether (3×10 mL). The extracts were dried with Na2SO4 and the mixture was filtered. Solvent was evaporated to give 2 as a white power (1.67 g, yield=86%)

Workup

  1. temperaturewas refluxed for 8 hours
  2. temperatureThe mixture was cooled
  3. extractionthe solution was extracted
  4. dry with materialThe extracts were dried with Na2SO4
  5. filtrationthe mixture was filtered
  6. customSolvent was evaporated
  7. customto give 2 as a white power (1.67 g, yield=86%)

Sources & evidence

ORD record
ord-a0e869470f0a40f094f7251af9f594e2
Source dataset
uspto-grants-2014_03
Patent number
US08679859B2

Reaction notes

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