Reaktion #574244

Reaktionsgleichung

3-bromophenyl boronic acid

methyl 2-chloronicotinate

sodium carbonate

toluene

→

methyl 2-[3-bromophenyl]nicotinate

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated 20 hours at 80°
2. 2
   Sonstigepartitioned between ethyl acetate and saturated sodium chloride solution
3. 3
   WaschenThe organic phase was washed with sodium chloride solution several times
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   SonstigeSolvent removal
6. 6
   Sonstigegave a crude product, which
7. 7
   Sonstigewas chromatographed on silica gel using 1:4 ethyl acetate

Vorschrift

A mixture of 4.02 g (20 mmole) of 3-bromophenyl boronic acid, 6.86 g (40 mmole) of methyl 2-chloronicotinate, 600 mg of tetrakis-(triphenylphosphine) palladium, 25 mL of 2M solution of sodium carbonate, 50 mL of toluene, and 13 mL of ethanol was heated 20 hours at 80°. The reaction mixture was cooled to r.t. and partitioned between ethyl acetate and saturated sodium chloride solution. The organic phase was washed with sodium chloride solution several times, and dried over anhydrous magnesium sulfate. Solvent removal gave a crude product, which was chromatographed on silica gel using 1:4 ethyl acetate:hexane mixture as eluant to give methyl 2-[3-bromophenyl]nicotinate as white amorphous powder.

Quelle