Reaktion #78090

Reaktionsgleichung

3-nitrophenylboronic acid

3-bromopyridine

potassium carbonate

1,3-propanediol

→

3-(3-nitrophenyl)pyridine

Ausbeute 84.3%

Lösungsmittel

dimethoxyethane

water

dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed under reduced pressure
2. 2
   workup.STIRRINGthe residue was stirred with additionally 200 ml water overnight
3. 3
   FiltrationThe precipitate was filtered off
4. 4
   Extraktionextracted with aqueous hydrochloric acid (4M, 300 ml)
5. 5
   workup.ADDITIONby addition of aqueous sodium hydroxide (12M)
6. 6
   FiltrationThe product was filtered off
7. 7
   Waschenwashed with water
8. 8
   Sonstigedried with suction

Vorschrift

A mixture of 3-nitrophenylboronic acid (50 g, 0.3 mol), 3-bromopyridine (48 ml, 0.5 mol), potassium carbonate (207 g, 1.5 mol), 1,3-propanediol (107 ml, 1.5 mol) and tetrakis(triphenylphosphine)palladium(0) (0.5 g) in a mixture of water (200 ml) and dimethoxyethane (400 ml) was stirred in a nitrogen atmosphere at 80° C. for 3 hours. After cooling the dimethoxyethane was removed under reduced pressure and the residue was stirred with additionally 200 ml water overnight. The precipitate was filtered off and extracted with aqueous hydrochloric acid (4M, 300 ml). The extract was rendered alkaline by addition of aqueous sodium hydroxide (12M). The product was filtered off, washed with water and dried with suction to yield 3-(3-nitrophenyl)pyridine (50.6 g, 84%).

Quelle