Phenol → HCID 118093763、化合物

HRID 1056969ノート

反応式

HRID 1056969 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1F.C(=O)([O-])[O-].[Cs+].[Cs+].[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CS(C)=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[O:25][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 3

HCID 996PhenolHCID 10796Cesium carbonateHCID 753658901-Bromo-2,4-difluoro-3-nitrobenzene

生成物 1

HCID 118093763HCID 118093763、化合物収率 34%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
20 °C

実験手順

A solution of 1-bromo-2,4-difluoro-3-nitrobenzene (0.128 g, 0.538 mmol) [Combi-Blocks, AN-3334] and cesium carbonate (0.211 g, 0.646 mmol) in dimethyl sulfoxide (0.59 mL) was treated with phenol (0.0609 g, 0.647 mmol) and stirred at 20° C. for 3 h, after which time the reaction mixture was diluted with water and ethyl acetate. Layers were separated and the organic layer was washed with brine, dried with magnesium sulfate, filtered, and concentrated to give a crude oil. Purification by preparative LCMS (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min) gave the desired product (57 mg, 34%) as a yellow solid.

後処理

  1. customLayers were separated
  2. washthe organic layer was washed with brine
  3. dry with materialdried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude oil
  7. customPurification by preparative LCMS (XBridge C18 column
  8. washeluting with a gradient of acetonitrile/water containing 0.1% trifluoroacetic acid, at flow rate of 60 mL/min)

出典と根拠

ORDレコード
ord-a7fbb52642824da5ac8fec360011feae
出典データセット
uspto-grants-2016_07
特許番号
US09399640B2

反応ノート

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