Réaction #2320124

Équation de réaction

6-bromo-3-methylpyridine

phenylboronic acid

triphenylphosphine

K2CO3

→

3-methyl-6-phenylpyridine

Rendement 84.1%

Solvants

dimethoxyethane

Conditions de réaction

Traitement

1. 1
   TempératureThe mixture was heated
2. 2
   Températureat reflux for 20 hours
3. 3
   ExtractionThe aqueous phase was extracted twice with 200 mL of ethyl acetate
4. 4
   ExtractionThe combined organic extractions
5. 5
   Extractionwere then extracted with brine
6. 6
   Séchagedried over magnesium sulfate
7. 7
   AutreThe filtrate was evaporated in vacuo
8. 8
   workup.DISTILLATIONthe resultant oil purified by Kugelehor distillation (190° C. @ 500 microns)

Mode opératoire

To a 2 L flask, 45.0 g (262 mmol) of 6-bromo-3-methylpyridine, 38.3 g (314 mmol) of phenylboronic acid, 1.47 g (6.54 mmol) of palladium acetate, 6.86 g (26.2 mmol) of triphenylphosphine and 353 mL of 2M K2CO3 were added to 405 mL of dimethoxyethane. The mixture was heated at reflux for 20 hours and cooled to room temperature. The aqueous phase was extracted twice with 200 mL of ethyl acetate. The combined organic extractions were then extracted with brine and dried over magnesium sulfate. The filtrate was evaporated in vacuo and the resultant oil purified by Kugelehor distillation (190° C. @ 500 microns) to give 37.2 g (84.1% yield) of 3-methyl-6-phenylpyridine as white solids.

Source