Reaction #43330

Reaction equation

2,5-dichloropyridine

potassium vinyltrifluoroborate

triethylamine

ethanol

→

title compound

Yield 69.0%

5-chloro-2-vinylpyridine

Yield 69.0%

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   Washby washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine
3. 3
   Dryingdrying over anhydrous sodium sulfate
4. 4
   ConcentrationConcentrating the solvent under reduced pressure
5. 5
   workup.DISTILLATIONthe resulting residue was distilled under reduced pressure (63° C., 8 mmHg)

Procedure

A mixture of 2,5-dichloropyridine (10.0 g), potassium vinyltrifluoroborate (10.86 g), dichloromethane complex (2.5 g) of dichloro-1,1′-bis(diphenylphosphino)-ferrocene palladium (II), triethylamine (14.13 mL) and ethanol (150 mL) was stirred overnight under reflux. After cooling the system to room temperature, ethyl acetate was added, followed by washing with saturated aqueous sodium hydrogencarbonate solution and saturated brine and drying over anhydrous sodium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was distilled under reduced pressure (63° C., 8 mmHg) to provide the title compound (6.50 g, 69%).

Source