Hexane → 2-(3-Fluorophenyl)-dibenzo[f,h]quinoxaline

HRID 1052917

反応式

HRID 1052917 の反応式
CCCCCC.C([Li])CCC.Br[C:13]1[CH:14]=[C:15]([F:19])[CH:16]=[CH:17][CH:18]=1.[N:20]1[C:29]2[C:24](=[C:25]3[CH:37]=[CH:36][CH:35]=[CH:34][C:26]3=[C:27]3[CH:33]=[CH:32][CH:31]=[CH:30][C:28]3=2)[N:23]=[CH:22][CH:21]=1>ClCCl.O.O1CCCC1>[F:19][C:15]1[CH:14]=[C:13]([C:22]2[CH:21]=[N:20][C:29]3[C:24](=[C:25]4[CH:37]=[CH:36][CH:35]=[CH:34][C:26]4=[C:27]4[CH:33]=[CH:32][CH:31]=[CH:30][C:28]4=3)[N:23]=2)[CH:18]=[CH:17][CH:16]=1

参加物

8

反応物 4

HCID 8058HexaneHCID 140821-Bromo-3-fluorobenzeneHCID 252644Dibenzo(f,h)quinoxalineHCID 178418339Butyllithium

生成物 1

HCID 577301122-(3-Fluorophenyl)-dibenzo[f,h]quinoxaline収率 23%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

First, under a nitrogen atmosphere, 27.5 mL (1.58 mol/L) of a hexane solution of n-butyllithium was dripped into a mixed solution of 6.87 g of 3-bromofluorobenzene and 40 mL of tetrahydrofuran at −78° C. Then, with the temperature maintained at −78° C., the mixture was stirred for 2 hours. To the obtained solution was added 7.54 g of dibenzo[f,h]quinoxaline in five additions at −78° C. The mixture was heated to room temperature, and stirred for 12 hours with the temperature maintained at room temperature. Water was added to this mixture and dichloromethane was used as an extraction solvent, so that an organic layer was extracted. The obtained organic layer was dried with anhydrous magnesium sulfate. The solution obtained by the drying was filtrated. The solvent of this solution was distilled off, and then, by recrystallization with ethanol, the organometallic complex of the present invention, Hdbq-3FP, which was the target substance, was obtained (a light-orange powder, yield: 23%). Synthesis scheme of Step 1 is shown in (a-2) below.

後処理

  1. temperatureThe mixture was heated to room temperature
  2. stirringstirred for 12 hours with the temperature
  3. temperaturemaintained at room temperature
  4. extractionwas extracted
  5. dry with materialThe obtained organic layer was dried with anhydrous magnesium sulfate
  6. customThe solution obtained by the drying
  7. filtrationwas filtrated
  8. distillationThe solvent of this solution was distilled off
  9. customby recrystallization with ethanol
  10. customwas obtained (a light-orange powder, yield: 23%)
  11. customSynthesis scheme of Step 1

出典と根拠

ORDレコード
ord-ed496725175d48599090f6b780714bb6
出典データセット
uspto-grants-2016_07
特許番号
US09391283B2

関連ノート

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