Iodine → HCID 72473125, compound

HRID 597895Notes

Reaction equation

HRID 597895 reaction equation
C([SnH](CCCC)CCCC)CCC.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]#[C:23][C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1.[I:31]I.S([O-])([O-])(=O)=S.[Na+].[Na+].[F-].[K+]>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[C:22]([I:31])=[CH:23][C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1

Participants

8

Reactant 5

HCID 807IodineHCID 5948TributylstannaneHCID 24477Sodium ThiosulfateHCID 522689Potassium FluorideHCID 58952506HCID 58952506, compound

Product 1

HCID 72473125HCID 72473125, compoundYield 83.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Tributyltin hydride (2.7 mL, 10 mmol) was added to a mixture of 2,4-dichloro-1-(4-chloro-phenylethynyl)-benzene (2.01 g, 7.13 mmol) and PdCl2(PPh3)2 (0.45 g, 0.64 mmol) in THF (70 mL) at room temperature and stirred for 1 h. Iodine crystals (2.7 g, 11 mmol) were added to the mixture at room temperature and stirred for 30 min. The mixture was then stirred with sodium thiosulfate aqueous solution and KF aqueous solution. The mixture was filtered through CELITE. The organic layer of the filtrate was separated and concentrated in vacuo. The residue was chromatographed (SiO2, hexane) to afford 2,4-dichloro-1-[2-(4-chloro-phenyl)-1-iodo-vinyl]-benzene as a light yellow solid (2.43 g, 83%).

Workup

  1. stirringstirred for 30 min
  2. filtrationThe mixture was filtered through CELITE
  3. customThe organic layer of the filtrate was separated
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed (SiO2, hexane)

Sources & evidence

ORD record
ord-9be3ed4f722b474487d8e0be9e699d47
Source dataset
uspto-grants-2011_03
Patent number
US07897601B2

Reaction notes

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