Cesium carbonate → 2-broMo-3-(difluoroMethoxy)pyridine

HRID 512073노트

반응식

HRID 512073 반응식
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[C:10]([F:15])([F:14])C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[Br:1][C:2]1[C:7]([O:8][CH:10]([F:15])[F:14])=[CH:6][CH:5]=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 230702-Bromo-3-pyridinolHCID 2734985Sodium chlorodifluoroacetate

생성물 1

HCID 580424482-broMo-3-(difluoroMethoxy)pyridine수율 35.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 2-bromo-3-pyridinol (1.26 g, 7.23 mmol) in DMF (35 mL) and water (5 mL) was added sodium chlorodifluoroacetate (2.93 g, 18.1 mmol) followed by cesium carbonate (4.71 g, 14.5 mmol). The reaction was heated to 100° C. for 36 hours before partitioning between EtOAc and water. The organic layer was collected, dried over magnesium sulfate and concentrated in vacuo. The residue was purified using silica gel column chromatography eluting with EtOAc:heptane 1:3 to afford the title compound as a colourless oil (570 mg, 35%).

후처리

  1. custombefore partitioning between EtOAc and water
  2. customThe organic layer was collected
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified
  6. washeluting with EtOAc:heptane 1:3

출처 및 근거

ORD 기록
ord-2e4d28557e22415e9b773334eea93f67
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102621B2

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