반응 #8304

반응 방정식

CH2Cl2

ethanol

2-bromo-5-fluoropyridine

sodium acetate

carbon monoxide

→

title compound

수율 58.0%

Ethyl 5-fluoropyridine-2-carboxylate

수율 58.0%

반응 조건

후처리

1. 1
   온도The vessel is cooled
2. 2
   기타volatiles removed in vacuo
3. 3
   기타the residue partitioned between ethyl acetate and water
4. 4
   추출The ethyl acetate extract
5. 5
   세척is washed with water and brine
6. 6
   건조dried over sodium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated
9. 9
   기타to give a dark solid
10. 10
    기타The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

실험 절차

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.

출처