Reaktion #42149

Reaktionsgleichung

2-chloropyridine

ortho-tolylboronic acid

potassium fluoride

→

2-ortho-tolylpyridine

Ausbeute 84.0%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeA 50-ml four-necked flask was equipped with a stirrer
2. 2
   workup.ADDITIONadded into the flask
3. 3
   SonstigeThe flask was purged with argon
4. 4
   workup.STIRRINGby stirring at 25° C. for 24 hours
5. 5
   SonstigeAfter the completion of the reaction, 10 ml of 10% aqueous sodium hydroxide solution
6. 6
   workup.ADDITIONwas added
7. 7
   Sonstigefollowed by separation
8. 8
   SonstigeThe organic phase was purified by column chromatography

Vorschrift

A 50-ml four-necked flask was equipped with a stirrer, a thermometer and a reflux condenser. 0.568 g (5 mmol) of 2-chloropyridine, 0.748 g (5.5 mmol) of ortho-tolylboronic acid, 0.011 g (0.05 mmol) of palladium (II) acetate, 0.959 g (17 mmol) of potassium fluoride and 10 ml of tetrahydrofuran were weighed in the flask, followed by stirring. Further, 0.026 g (0.05 mmol) of tri-tert-butylphosphonium tetraphenylborate obtained in Example A-1 was weighed in air and added into the flask. The flask was purged with argon, followed by stirring at 25° C. for 24 hours. After the completion of the reaction, 10 ml of 10% aqueous sodium hydroxide solution was added, followed by separation. The organic phase was purified by column chromatography to afford 0.711 g of 2-ortho-tolylpyridine (yield: 84 mol % based on 2-chloropyridine). The identification of the product was made by mass spectroscopy.

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