Cesium carbonate → 1-Bromo-4-(2,4-difluorophenoxy)-2-fluoro-5-nitrobenzene

HRID 633522

반응식

HRID 633522 반응식
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[F:12].C(=O)([O-])[O-].[Cs+].[Cs+].[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[OH:27]>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([F:11])=[CH:4][C:3]=1[O:27][C:21]1[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=1[F:19].[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:27][C:21]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=2[F:19])=[CH:4][C:3]=1[F:12]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 1230512,4-DifluorophenolHCID 2230781-Bromo-2,4-difluoro-5-nitrobenzene

생성물 2

HCID 904159951-Bromo-4-(2,4-difluorophenoxy)-2-fluoro-5-nitrobenzeneHCID 904186191-Bromo-2-(2,4-difluorophenoxy)-4-fluoro-5-nitrobenzene

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A mixture of 1-bromo-2,4-difluoro-5-nitrobenzene (0.5 g, 2.10 mmol) and cesium carbonate (0.685 g, 2.10 mmol) in DMSO (10.50 mL) was treated dropwise with 2,4-difluorophenol (0.273 g, 2.10 mmol), stirred for 60 minutes at ambient temperature and partitioned between ethyl acetate and water, adjusting the pH to 6 with 1 M HCl. The organic layer was washed with water, saturated aqueous sodium chloride, dried (MgSO4), filtered, and concentrated. Purification by chromatography (silica gel, 0-30% ethyl acetate in heptanes) afforded the title compound and 1-bromo-4-(2,4-difluorophenoxy)-2-fluoro-5-nitrobenzene as an inseparable mixture (0.59 g, 81%).

후처리

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water, saturated aqueous sodium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (silica gel, 0-30% ethyl acetate in heptanes)

출처 및 근거

ORD 기록
ord-5e93caf2891d47e6b8f113ebe17841b7
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321764B2

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