反応 #8304

反応方程式

CH2Cl2

ethanol

2-bromo-5-fluoropyridine

sodium acetate

carbon monoxide

→

title compound

収率 58.0%

Ethyl 5-fluoropyridine-2-carboxylate

収率 58.0%

反応条件

後処理

1. 1
   温度The vessel is cooled
2. 2
   その他volatiles removed in vacuo
3. 3
   その他the residue partitioned between ethyl acetate and water
4. 4
   抽出The ethyl acetate extract
5. 5
   洗浄is washed with water and brine
6. 6
   乾燥dried over sodium sulfate
7. 7
   ろ過filtered
8. 8
   その他evaporated
9. 9
   その他to give a dark solid
10. 10
    その他The residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

実験手順

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.

出典