Ethanol → Ethyl 5-(difluoromethoxy)picolinate

HRID 15045

反応式

HRID 15045 の反応式
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]

参加物

8

反応物 4

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

生成物 1

HCID 68430338Ethyl 5-(difluoromethoxy)picolinate収率 80%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 178418416HCID 178418416、化合物溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-c61847675b0b4ea78310640084b42d11
出典データセット
uspto-grants-2010_06
特許番号
US07732456B2

関連ノート

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