Réaction #8304

Équation de réaction

CH2Cl2

ethanol

2-bromo-5-fluoropyridine

sodium acetate

carbon monoxide

→

title compound

Rendement 58.0%

Ethyl 5-fluoropyridine-2-carboxylate

Rendement 58.0%

Conditions de réaction

Traitement

1. 1
   TempératureThe vessel is cooled
2. 2
   Autrevolatiles removed in vacuo
3. 3
   Autrethe residue partitioned between ethyl acetate and water
4. 4
   ExtractionThe ethyl acetate extract
5. 5
   Lavageis washed with water and brine
6. 6
   Séchagedried over sodium sulfate
7. 7
   Filtrationfiltered
8. 8
   Autreevaporated
9. 9
   Autreto give a dark solid
10. 10
    AutreThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

Mode opératoire

A mixture of 2-bromo-5-fluoropyridine (5.00 g, 28.4 mmol), sodium acetate (9.33 g, 114 mmol), and 1-1′bis(diphenylphosphino)ferrocene]dichloropalladium(II):CH2Cl2 (0.464 g, 0.57 mmol) in ethanol (80 mL) in a Parr® high pressure stainless steel reactor vessel is placed under an atmosphere of 50 psi carbon monoxide and heated at 80-100° C. for 4 h. The vessel is cooled, volatiles removed in vacuo, and the residue partitioned between ethyl acetate and water. The ethyl acetate extract is washed with water and brine, dried over sodium sulfate, filtered, and evaporated to give a dark solid. The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes) to yield the title compound 2.8 g (58%) as a white solid that is recrystallized from hexanes to give white crystals: mp 61-63° C.

Source