乙醇 → 5-氟吡啶-2-甲酸乙酯

HRID 8208

反应方程式

HRID 8208 反应方程式
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][N:3]=1.[C:9]([O-:12])(=[O:11])C.[Na+].C(Cl)Cl.[C]=O.[CH2:19](O)[CH3:20]>Cl[Pd]Cl>[F:8][C:5]1[CH:6]=[CH:7][C:2]([C:9]([O:12][CH2:19][CH3:20])=[O:11])=[N:3][CH:4]=1

参与物

7

反应物 5

HCID 702乙醇HCID 6344二氯甲烷HCID 517045醋酸钠HCID 27831712-溴-5-氟吡啶HCID 178418416HCID 178418416，化合物

产物 1

HCID 109866755-氟吡啶-2-甲酸乙酯收率 58%

试剂、催化剂与溶剂 1

HCID 24290氯化钯催化剂

反应条件

温度
90 °C

实验过程

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.

后处理

  1. temperatureThe vessel is cooled
  2. customvolatiles removed in vacuo
  3. customthe residue partitioned between ethyl acetate and water
  4. extractionThe ethyl acetate extract
  5. washis washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give a dark solid
  10. customThe residue is chromatographed on SiO2 (10% ethyl acetate/hexanes)

来源与证据

ORD记录
ord-61b52ed67bce44c09e6ab3755fd6da79
来源数据集
uspto-grants-2006_08
专利号
US07087626B2

关联笔记

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