Reaktion #574253

Reaktionsgleichung

3-bromo-5-formyl-phenylboronic acid

methyl 2-chloro-nicotinate

ethanol

sodium bicarbonate

→

desired product

Methyl 2-[3'-bromo-5'-formylphenyl]nicotinate

Lösungsmittel

ethyl acetate

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated 20 hrs at 80° under nitrogen
2. 2
   Waschenthe reaction mixture was washed with saturated NaCl solution
3. 3
   TrocknenThe organic phase was dried over anhydrous MgSO4
4. 4
   SonstigeSolvent removal
5. 5
   Sonstigegave a crude product which
6. 6
   Sonstigewas purified on silica

Vorschrift

A mixture of 1.14 g (5 mmoles) of 3-bromo-5-formyl-phenylboronic acid, 1.715 g (10 mmoles) of methyl 2-chloro-nicotinate, 100 mg of tetrakis-(triphenyl phosphine)palladium, 2.5 mL of ethanol, 10 mL of 2M sodium bicarbonate solution, and 10 mL of toluene was heated 20 hrs at 80° under nitrogen. After diluting with ethyl acetate, the reaction mixture was washed with saturated NaCl solution. The organic phase was dried over anhydrous MgSO4. Solvent removal gave a crude product which was purified on silica using ethyl acetate:hexane mixture as solvent to give the desired product as a solid.

Quelle