1,2-Diiodoethane → 3-Bromo-5-iodo-1,1'-biphenyl

HRID 1014903Notes

Reaction equation

HRID 1014903 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:6](Br)[CH:7]=1.BrC1C=C([I:23])C=C(Br)C=1.C1(B(O)O)C=CC=CC=1.C([Li])CCC.ICCI.S([O-])(O)=O.[Na+]>C(Cl)Cl.O.CCCCCC.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[C:6]([I:23])[CH:7]=1

Participants

11

Reactant 6

HCID 122241,2-DiiodoethaneHCID 66827Phenylboronic AcidHCID 30149331,1'-Biphenyl, 3,5-dibromo-HCID 110684371,3-DIBROMO-5-IODOBENZENEHCID 23665763Sodium BisulfiteHCID 178418339Butyllithium

Product 1

HCID 156615263-Bromo-5-iodo-1,1'-biphenylYield 85%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

Under the atmosphere of argon, 20 g of 3,5-dibromobiphenyl synthesized from 3,5-dibromoiodobenzene and phenylboronic acid was dissolved into 200 ml of anhydrous THF, and the resultant solution was cooled at −70° C. To the cooled solution, 42 ml of a 1.6 M hexane solution of normal-butyllithium was added dropwise, and the resultant mixture was stirred for 30 minutes. Then, 19 g of 1,2-diiodoethane was added, and the obtained mixture was stirred for 5 hours. After the mixture was left standing for one night, water and methylene chloride were added. Then, sodium hydrogensulfite was added until dark brown color of the reaction mixture turned to yellow color. The organic layer was obtained by extraction, washed with water and a saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate, and the solvent was removed using an evaporator. The obtained residue was purified in accordance with the silica gel column chromatography (the developing solvent: hexane), and 19.5 g of 3-bromo-5-iodobiphenyl was obtained as a colorless oil (the yield: 85%).

Workup

  1. waitAfter the mixture was left
  2. waitstanding for one night
  3. customThe organic layer was obtained by extraction
  4. washwashed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried with anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customan evaporator
  8. customThe obtained residue was purified in accordance with the silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-ae8163c44727444f878df7c98f50174d
Source dataset
uspto-grants-2011_07
Patent number
US07985491B2

Reaction notes

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