Ethanol → Ethyl 5-fluoropyridine-2-carboxylate

HRID 8208

반응식

HRID 8208 반응식
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

참가 물질

7

반응물 5

HCID 702EthanolHCID 6344DichloromethaneHCID 517045Sodium AcetateHCID 27831712-Bromo-5-fluoropyridineHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 10986675Ethyl 5-fluoropyridine-2-carboxylate수율 58%

시약·촉매·용매 1

HCID 24290Palladium Chloride촉매

반응 조건

온도
90 °C

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-61b52ed67bce44c09e6ab3755fd6da79
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087626B2

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