Reaktion #88367

Reaktionsgleichung

2-fluoro-3-nitro-benzaldehyde

sodium chlorite

1,4-dioxane

sulfamic acid

→

desired compound

Ausbeute 13.5%

2-fluoro-3-nitro-benzoic acid

Ausbeute 13.5%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   WaschenThe organic layer is washed with water
3. 3
   Trocknenbrine, dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenthe filtrate is concentrated under vacuum
6. 6
   SonstigeThe resulting material is purified on column chromatography
7. 7
   Wascheneluting with methanol and dichloromethane
8. 8
   Einengenconcentrated under vacuum
9. 9
   FiltrationThe resulting solid is collected by filtration

Vorschrift

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.

Quelle