Cesium carbonate → Benzonitrile, 4-(2-bromo-4-nitrophenoxy)-

HRID 633530ノート

反応式

HRID 633530 の反応式
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1F.[OH:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:12][C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=1

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 130194-CyanophenolHCID 696992-Bromo-1-fluoro-4-nitrobenzene

生成物 1

HCID 1491136Benzonitrile, 4-(2-bromo-4-nitrophenoxy)-収率 110%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-bromo-1-fluoro-4-nitrobenzene (2.20 g, 10 mmol), 4-hydroxybenzonitrile (1.31 g, 11 mmol), and cesium carbonate (3.58 g, 11 mmol) in DMSO (20 mL) was heated at 90° C. for 2 hours. After cooling, the reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 3.19 g (110%) of the title compound.

後処理

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between water and ethyl acetate
  3. extractionThe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-20cb792ddcd147e6b8a3f796bea253af
出典データセット
uspto-grants-2016_04
特許番号
US09321764B2

反応ノート

読み込み中…