Hydrochloric Acid → 4-Azidotetrafluorobenzoic acid

HRID 1190786Notes

Reaction equation

HRID 1190786 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 85.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2 (1.67 g, 6.7 mmol) with 10% (w/v) NaOH (4 mL) in MeOH (20 mL) was stirred overnight at room temperature. The solution was acidified by 2 M HCl in an ice bath to pH<1 and extracted with CHCl3 (3×10 mL). The extracts were dried with Na2SO4, and the mixture was filtered. Solvent was evaporated to give 3 as a white solid (1.35 g, yield=85%)

Workup

  1. extractionextracted with CHCl3 (3×10 mL)
  2. dry with materialThe extracts were dried with Na2SO4
  3. filtrationthe mixture was filtered
  4. customSolvent was evaporated

Sources & evidence

ORD record
ord-b4af7821f2a24bf68c29b29db80785c9
Source dataset
uspto-grants-2014_03
Patent number
US08679859B2

Reaction notes

Loading…