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

HRID 228138

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HRID 228138 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

HCID 866100341-(3-Bromo-4-iodophenyl)pyrene수율 84.3%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-70 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-4c62a0fea0c04ffa9b64c76ce3f80365
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560604B2

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