3,5-Dibromotoluene → HCID 20643063, compound

HRID 1178789Notes

Reaction equation

HRID 1178789 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6](Br)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)CCC.[Cl-].[Li+].[F-].[K+]>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.C1(C)C=CC=CC=1>[N:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:2]1[CH:3]=[C:4]([CH3:9])[CH:5]=[C:6]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:15][N:16]=2)[CH:7]=1

Participants

7

Reactant 4

HCID 153613,5-DibromotolueneHCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 6077842-(Tributylstannyl)pyridine

Product 1

HCID 20643063HCID 20643063, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Procedure

A tridentate ligand, 3,5-di(2-pyridyl)toluene was synthesized as follows. Specifically, 3,5-dibromotoluene (6.9 g; 20 mmol), 2-tri-n-butylstannylpyridine (26.9 g; 73 mmol), bis(triphenylphosphine)palladium dichloride (1.55 g; 2.2 mmol), and lithium chloride (11.7 g; 276 mmol) were added to 130 ml of toluene and the mixture was refluxed for 2 days. After cooling, 50 ml of saturated potassium fluoride solution was added. The precipitated solid was separated by filtration, washed with a small amount of cooled toluene (20 ml×3), and vacuum dried. The obtained solid was placed to a mixed solution of dichloromethane and NaHCO3, and washed well. The organic layer was separated, was dried over MgSO4 powder, and then the solvent was removed by evaporation. Next, the solid was recrystallized from dichloromethane to obtain 2.2 g of grey solid of 3,5-di(2-pyridyl)toluene of interest.

Workup

  1. temperaturethe mixture was refluxed for 2 days
  2. temperatureAfter cooling
  3. customThe precipitated solid was separated by filtration
  4. washwashed with a small amount of cooled toluene (20 ml×3), and vacuum
  5. customdried
  6. washwashed well
  7. customThe organic layer was separated
  8. dry with materialwas dried over MgSO4 powder
  9. customthe solvent was removed by evaporation
  10. customNext, the solid was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-1db6e831e1f54d22be2904df8ea2dc7a
Source dataset
uspto-grants-2007_10
Patent number
US07276617B2

Reaction notes

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