1,2-Diiodoethane → 1-(3-Bromo-4-iodophenyl)pyrene

HRID 228138

反応式

HRID 228138 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][CH:16]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:5]=[C:6](Br)[CH:7]=1.C1(B(O)O)C2C3=C4C(=CC=2)C=CC=C4C=CC3=CC=1.CCCCCC.C([Li])CCC.[I:55]CCI.S(=O)(O)[O-].[Na+]>C(Cl)Cl.O.O1CCCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:22]3[C:23]4=[C:24]5[C:19](=[CH:20][CH:21]=3)[CH:18]=[CH:17][CH:16]=[C:15]5[CH:14]=[CH:13][C:12]4=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[I:55]

参加物

9

反応物 5

HCID 122241,2-DiiodoethaneHCID 5084102Pyren-1-ylboronic acidHCID 23665763Sodium BisulfiteHCID 714247391-(3,5-Dibromophenyl)pyreneHCID 178418244HCID 178418244、化合物

生成物 1

HCID 866100341-(3-Bromo-4-iodophenyl)pyrene収率 84.3%

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
-70 °C

実験手順

Under the atmosphere of argon gas, 9 g of 1-(3,5-dibromophenyl)pyrene synthesized from 3,5-diboromoiodobenzene and 1-pyrenyl boronic acid was dissolved into 100 ml of anhydrous tetrahydrofuran (THF) and cooled down to −70° C. 14 ml of 1.6M n-butyllithium hexane solution was dropped therein and the resultant was stirred for 30 minutes. 5.9 g of 1,2-diiodoethane was added therein and the resultant was stirred for 5 hours. After the resultant was left overnight, water and methylene chloride were added therein, and then sodium bisulfite was added therein until the burned umber of the reaction solution was changed to yellow. The organic layer was extracted therefrom, and then it was washed by water and saturated salt water. Subsequently the organic layer was dried by using anhydrous sodium sulfate, and then the solvent was removed by distillation. The residue was refined through a silica gel chromatography (developing solvent: toluene/hexane=1/3) and then 8.4 g of 1-(3-bromo-4-iodophenyl)pyrene of cream color solid was obtained (Yield: 84%).

後処理

  1. stirringthe resultant was stirred for 5 hours
  2. waitAfter the resultant was left overnight
  3. extractionThe organic layer was extracted
  4. washit was washed by water and saturated salt water
  5. customSubsequently the organic layer was dried
  6. customthe solvent was removed by distillation

出典と根拠

ORDレコード
ord-4c62a0fea0c04ffa9b64c76ce3f80365
出典データセット
uspto-grants-2009_07
特許番号
US07560604B2

関連ノート

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