Sodium Carbonate → 1,1':4',1''-Terphenyl, 4-iodo-

HRID 1828405Notes

Reaction equation

HRID 1828405 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:15]1(OB(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 763484,4'-Diiodo-1,1'-biphenylHCID 78412Phenyl dihydrogen orthoborate

Product 1

HCID 111110491,1':4',1''-Terphenyl, 4-iodo-Yield 35%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

The compound was prepared under Suzuki reaction conditions. 4,4′-diiodo-biphenyl (1.0 g, 2.46 mmol), phenyl boric acid (0.24 g, 1.970 mmol), tetrakis(triphenylphosphine)palladium (0.085 g, 0.074 mmol), 2M-sodium carbonate (12.3 ml) and toluene (76 ml) were simultaneously mixed, freezed under liquid nitrogen, evacuated by a vacuum pump and then warmed to room temperature to be melted. This procedure was repeated twice, followed by injection of nitrogen. The mixed solution was refluxed for 2 days and cooled to room temperature. Thereafter, a small amount of distilled water was added, and the organic layer was filtered three times with dichloromethane, dried with sodium sulfate. Then, the dichloromethane was concentrated under reduced pressure. Purification by silica gel chromatography using 1% dichloromethane in hexane gave 4″-iodo-[1,1′;4′,1″]terphenyl (Yield: 0.245 g, 35%). The structure of the product was identified through the NMR spectrum and mass spectrum. FIG. 6 shows the mass spectrum of 4″-iodo-[1,1′;4′,1″]terphenyl.

Workup

  1. customThe compound was prepared under Suzuki reaction conditions
  2. customevacuated by a vacuum pump
  3. temperatureThe mixed solution was refluxed for 2 days
  4. temperaturecooled to room temperature
  5. additionThereafter, a small amount of distilled water was added
  6. filtrationthe organic layer was filtered three times with dichloromethane
  7. dry with materialdried with sodium sulfate
  8. concentrationThen, the dichloromethane was concentrated under reduced pressure
  9. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-3722f70ca65948e3a50a4c1cb04e2068
Source dataset
uspto-grants-2006_06
Patent number
US07057074B2

Reaction notes

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