Reaktion #86090

Reaktionsgleichung

potassium acetate hydrate

sodium carbonate decahydrate

3,5-dibromopyridine

2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

→

3-bromo-5-isopropenyl-pyridine

Ausbeute 52.0%

Lösungsmittel

Acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   ExtraktionThe aqueous layer was extracted with EtOAc
3. 3
   EinengenThe combined organic layer was concentrated
4. 4
   SonstigeThe residue was purified on silica
5. 5
   Wascheneluted with 0 to 10% MeOH in DCM

Vorschrift

A mixture of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct; 98.0 mass %, potassium acetate hydrate (7.4997 mmol; 3.7 mL), sodium carbonate decahydrate (7.4997 mmol; 3.7 mL), Acetonitrile (15 mL) and 3,5-dibromopyridine (4.9998 mmol; 1184.4 mg) in 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (4.9998 mmol; 840.0 mg; 0.940 mL) in a pressure tube was heated under microwave at 120° C. for 3 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layer was concentrated. The residue was purified on silica eluted with 0 to 10% MeOH in DCM to afford 3-bromo-5-isopropenyl-pyridine as a dark tan solid (512.6 mg, 52%).

Quelle