Hydrochloric Acid → 4-Azidotetrafluorobenzoic acid

HRID 750407Notes

Reaction equation

HRID 750407 reaction equation
[N:1]([C:4]1[C:13]([F:14])=[C:12]([F:15])[C:7]([C:8]([O:10]C)=[O:9])=[C:6]([F:16])[C:5]=1[F:17])=[N+:2]=[N-:3].[OH-].[Na+].Cl>CO>[N:1]([C:4]1[C:5]([F:17])=[C:6]([F:16])[C:7]([C:8]([OH:10])=[O:9])=[C:12]([F:15])[C:13]=1[F:14])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 129750Methyl 4-azido-2,3,5,6-tetrafluorobenzoate

Product 1

HCID 27625784-Azidotetrafluorobenzoic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.009 g (4.0 mmol) of methyl 4-azido-2,3,5,6-tetrafluorobenzoate in 4 mL (10 mmol) of 10% NaOH, and 20 mL of methanol was stirred at room temperature for 12 hours. This solution was carefully acidified in an ice bath with approximately 10 mL of 1.2 M HCl to a pH<2. The acidified solution was extracted with chloroform (3×10 mL), dried over anhydrous sodium sulfate, and evaporated to afford 4-azidotetrafluorobenzoic acid (0.9181 g, 96%) as white flakes, mp 141.6-142.8° C.

Workup

  1. extractionThe acidified solution was extracted with chloroform (3×10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-a36e1171e98646809ab2f3c55bf2ba71
Source dataset
uspto-grants-2008_07
Patent number
US07405034B2

Reaction notes

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