Sulfamic Acid → 2-Fluorobenzoic acid

HRID 1178030Notes

Reaction equation

HRID 1178030 reaction equation
Cl([O-])=O.[Na+].[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].S(=O)(=O)([OH:16])N>O.CC(C)=O>[F:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[C:8]([OH:16])=[O:9]

Participants

6

Reactant 3

HCID 5987Sulfamic AcidHCID 67970o-FluorobenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 99352-Fluorobenzoic acidYield 86%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

Sodium chlorite (1.45 g, 16.11 mmol) in 2 mL water was added at 0° C. to 2-fluoro-benzaldehyde (0.5 g, 4.03 mmol) in 5 mL acetone. After 5 minutes, sulphamic acid (1.17 gm, 12.086 mmol) was added and the resulting mixture was stirred at 0° C. for 20 minutes. Water was then added, and the resulting precipitate was filtered under reduced pressure. The aqueous layer was extracted with EtOAc and washed with brine. The organic phase was dried over Na2SO4 and concentrated under reduced pressure to afford 2-fluorobenzoic acid in 86% yield.

Workup

  1. filtrationthe resulting precipitate was filtered under reduced pressure
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washwashed with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27c0527133cf42a4af9f0b24160c75ef
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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