Ethanol → Ethyl 5-(difluoromethoxy)picolinate

HRID 15045

반응식

HRID 15045 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 68430338Ethyl 5-(difluoromethoxy)picolinate수율 80%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매HCID 178418416HCID 178418416, 화합물용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-c61847675b0b4ea78310640084b42d11
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732456B2

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