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

HRID 228138

Reaction equation

HRID 228138 reaction equation
[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]

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-4c62a0fea0c04ffa9b64c76ce3f80365
Source dataset
uspto-grants-2009_07
Patent number
US07560604B2

Linked notes

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