Sulfamic Acid → 2-Fluoro-3-nitrobenzoic acid

HRID 60089Notes

Reaction equation

HRID 60089 reaction equation
[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].Cl([O-])=[O:14].[Na+].O1CCOCC1.S(=O)(=O)(O)N>O>[F:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]([OH:14])=[O:5]

Participants

6

Reactant 4

HCID 5987Sulfamic AcidHCID 312751,4-DioxaneHCID 104873252-Fluoro-3-nitrobenzaldehydeHCID 23668197Sodium Chlorite

Product 1

HCID 186729922-Fluoro-3-nitrobenzoic acidYield 13.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In a round bottom flask, 2-fluoro-3-nitro-benzaldehyde (15, 1.02 g, 6.03 mmol) is combined with sodium chlorite (1.26 g, 11.15 mmol), 60 mL of 1,4-dioxane, 20 mL of water, and sulfamic acid (4.47 g, 46.0 mmol) and the reaction is stirred at room temperature for 30 minutes. The mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water, then brine, dried over magnesium sulfate, filtered and the filtrate is concentrated under vacuum. The resulting material is purified on column chromatography, eluting with methanol and dichloromethane. Appropriate fractions are combined and concentrated under vacuum, then suspended in dichloromethane. The resulting solid is collected by filtration to provide the desired compound (16, 151 mg). MS (ESI)[M−H+]−=184.4.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer is washed with water
  3. dry with materialbrine, dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate is concentrated under vacuum
  6. customThe resulting material is purified on column chromatography
  7. washeluting with methanol and dichloromethane
  8. concentrationconcentrated under vacuum
  9. filtrationThe resulting solid is collected by filtration

Sources & evidence

ORD record
ord-bc1e2c425c6e42a5b0a1a83262664a25
Source dataset
uspto-grants-2016_09
Patent number
US09440969B2

Reaction notes

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