Reaktion #41552

Reaktionsgleichung

sodium carbonate

3-bromo-4-fluoro-nitrobenzene

1-(t-butoxycarbonyl)pyrrole-2-boronic acid

sodium bicarbonate

→

t-butyl 2-(2-fluoro-5-nitro-phenyl)-pyrrole-1-carboxylate

Lösungsmittel

dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe reaction liquid
2. 2
   Temperaturwas heated overnight
3. 3
   Temperaturunder reflux
4. 4
   Extraktionthis was extracted with ethyl acetate
5. 5
   WaschenThe organic layer was washed with water and saturated saline in order
6. 6
   Trocknendried with anhydrous sodium sulfate
7. 7
   SonstigeThe solvent was evaporated away under reduced pressure
8. 8
   Sonstigethe resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=20/1)
9. 9
   Sonstigeto obtain the entitled compound as a yellow oily substance

Vorschrift

1.1 g of tetrakis-triphenylphosphine palladium and 4.2 g of sodium carbonate were added to a solution of 4.3 g of 3-bromo-4-fluoro-nitrobenzene and 5.0 g of 1-(t-butoxycarbonyl)pyrrole-2-boronic acid in a mixture of 130 ml of dimethoxyethane and 22 ml of water, and the reaction liquid was heated overnight under reflux. Aqueous saturated sodium bicarbonate was added to the reaction liquid, and this was extracted with ethyl acetate. The organic layer was washed with water and saturated saline in order, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: hexane/ethyl acetate=20/1) to obtain the entitled compound as a yellow oily substance.

Quelle