Ethanol → Ethyl 5-(difluoromethoxy)picolinate

HRID 15045

Reaktionsgleichung

Reaktionsgleichung von HRID 15045
CN([CH:4]=[O:5])C.[CH2:6]([OH:8])[CH3:7].Br[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[CH:12][N:11]=1.C(N(CC)CC)C>[C]=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH2:6]([O:8][C:4]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[CH:12][N:11]=1)=[O:5])[CH3:7]

Komponenten

8

Edukt 4

HCID 702EthanolHCID 6228DimethylformamideHCID 8471TriethylamineHCID 231205792-Bromo-5-(difluoromethoxy)pyridine

Produkt 1

HCID 68430338Ethyl 5-(difluoromethoxy)picolinateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 178418416HCID 178418416, VerbindungLösungsmittel

Versuchsvorschrift

A DMF (15 mL)-ethanol (15 mL) mixed solvent solution of 2-bromo-5-difluoromethoxypyridine (1.32 g, 5.89 mmols), palladium acetate (132 mg, 0.59 mmol), 1,1′-bis(diphenylphosphino)ferrocene (654 mg, 1.18 mmols) and triethylamine (1.6 mL, 11.8 mmols) was stirred overnight at 50° C. in carbon monoxide atmosphere. The reaction liquid was cooled to room temperature and the solvent was concentrated under reduced pressure. Ethyl acetate was added to the resulting residue, followed by washing with water and drying over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=4:1-3:2) to provide the title compound (1.03 g, 80%).

Aufarbeitung

  1. customThe reaction liquid
  2. concentrationthe solvent was concentrated under reduced pressure
  3. additionEthyl acetate was added to the resulting residue
  4. washby washing with water
  5. dry with materialdrying over anhydrous magnesium sulfate
  6. concentrationConcentrating the solvent under reduced pressure
  7. customthe residue was purified on silica gel column chromatography (C-300, hexane:ethyl acetate=4:1-3:2)

Quellen und Nachweise

ORD-Eintrag
ord-c61847675b0b4ea78310640084b42d11
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732456B2

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