Ethanol → Ethyl 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylate

HRID 1532560

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HRID 1532560 반응식
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[CH2:13]([OH:15])C.[C]=[O:17].C(N([CH2:23][CH3:24])CC)C>[Cl-].[Cl-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd+2]>[Cl:8][C:7]1[C:2]([C:13]([O:15][CH2:23][CH3:24])=[O:17])=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 178418416HCID 178418416, 화합물

생성물 1

HCID 22013558Ethyl 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylate수율 85%

시약·촉매·용매 1

HCID 84124Bis(triphenylphosphine)palladium chloride촉매

반응 조건

온도
25 °C

실험 절차

An autoclave is loaded with 200 g of 2,3-dichloro-5-trifluoromethylpyridine, 1.85 l of ethanol, 260 ml of triethylamine and 6.5 g of palladium bis(triphenylphosphine)dichloride (PdCl2(PPh3)2). 110 bar of carbon monoxide are then forced in at 25° C. and the mixture is kept at 110° C. for 24 hours. After cooling to 25° C., the crude mixture is concentrated to a thick slurry, which is then partitioned between dilute sodium chloride solution and ethyl acetate. After extraction by shaking and separation of the phases, the ethyl acetate phase is washed with water, dried over sodium sulfate and concentrated to dryness. The crude product is distilled under a high vacuum at 0.035 mbar. 200 g of the desired product are obtained as a yellow oil of boiling point 67-70° C./0.035 mbar (yield 85% of theory)

후처리

  1. customare then forced in at 25° C.
  2. concentrationthe crude mixture is concentrated to a thick slurry, which
  3. customis then partitioned between dilute sodium chloride solution and ethyl acetate
  4. extractionAfter extraction
  5. customseparation of the phases
  6. washthe ethyl acetate phase is washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated to dryness
  9. distillationThe crude product is distilled under a high vacuum at 0.035 mbar

출처 및 근거

ORD 기록
ord-d29fa9fbecd24dc2b9ef39ec3d0cf1e9
출처 데이터셋
uspto-grants-2001_03
특허 번호
US06204221B1

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