تفاعل #8304

معادلة التفاعل

CH2Cl2

ethanol

2-bromo-5-fluoropyridine

sodium acetate

carbon monoxide

→

title compound

المردود 58.0%

Ethyl 5-fluoropyridine-2-carboxylate

المردود 58.0%

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe vessel is cooled
2. 2
   أخرىvolatiles removed in vacuo
3. 3
   أخرىthe residue partitioned between ethyl acetate and water
4. 4
   استخلاصThe ethyl acetate extract
5. 5
   غسيلis washed with water and brine
6. 6
   تجفيفdried over sodium sulfate
7. 7
   ترشيحfiltered
8. 8
   أخرىevaporated
9. 9
   أخرىto give a dark solid
10. 10
    أخرىThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

الإجراء التجريبي

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.

المصدر