Sodium Carbonate → HCID 24744244、化合物

HRID 735896ノート

反応式

HRID 735896 の反応式
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[O:6][C:5]=2[C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[N+:24]([C:21]1[CH:22]=[CH:23][C:18]([C:4]2[C:5]3[O:6][C:7]4[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=4[C:9]=3[CH:1]=[CH:2][CH:3]=2)=[CH:19][CH:20]=1)([O-:26])=[O:25]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 114661-Bromo-4-nitrobenzeneHCID 2734328Dibenzofuran-4-boronic acid

生成物 1

HCID 24744244HCID 24744244、化合物収率 62.6%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 22272177Toluene water溶媒

反応条件

温度
0 °C

実験手順

To a mixture of dibenzofuran-4-boronic acid (30 g, 0.14 mol), 4-bromonitrobenzene (25.7 g, 0.127 mol), sodium carbonate (150 g) in toluene/water (500 mL/500 mL) was added tetrakis(triphenylphosphine)palladium(0) (8.2 g, 0.7 mol %) and the resulting reaction mixture was refluxed for 20 h under N2 atmosphere. The toluene layer was separated and concentrated to 200 mL. The concentrated solution was cooled to 0° C. and filtered off. The collected solid was dried and dissolved in chloroform and the obtained solution was filtered through celite bed to remove insoluble materials. The filtrate was concentrated under vacuum to give the title compound (23 g, 58%).

後処理

  1. customthe resulting reaction mixture
  2. temperaturewas refluxed for 20 h under N2 atmosphere
  3. customThe toluene layer was separated
  4. concentrationconcentrated to 200 mL
  5. filtrationfiltered off
  6. customThe collected solid was dried
  7. dissolutiondissolved in chloroform
  8. filtrationthe obtained solution was filtered through celite bed
  9. customto remove insoluble materials
  10. concentrationThe filtrate was concentrated under vacuum

出典と根拠

ORDレコード
ord-ca999d04824049c6853ada4b925dfbbb
出典データセット
uspto-grants-2009_09
特許番号
US07592477B2

反応ノート

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