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

HRID 633522

反応式

HRID 633522 の反応式
[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]

参加物

6

反応物 3

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

生成物 2

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5e93caf2891d47e6b8f113ebe17841b7
出典データセット
uspto-grants-2016_04
特許番号
US09321764B2

関連ノート

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