Potassium Iodide → HCID 22066270, compound

HRID 585420Notes

Reaction equation

HRID 585420 reaction equation
[Br:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10](O)[CH:9]=2)=[CH:6][C:5]([OH:15])=[CH:4][CH:3]=1.[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[C:25](=[O:28])([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:28][CH2:25][CH2:8][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH:9]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 22066276HCID 22066276, compound

Product 1

HCID 22066270HCID 22066270, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

6-bromo-biphenyl-3,3′-diol (5.92 g, 22.43 mmol) prepared in Example 2, 1-octylbromide, potassium carbonate (18.60 g, 134.56 mmol) and potassium iodide (3.72 g, 22.43 mmol) were dissolved in dimethylformamide (60 ml), followed by heating for about 24 hours at about 150° C. After cooling to room temperature, distilled water was added to the resultant and stirred for about 10 minutes, followed by filtering three times with hexane, washing three times with distilled water, drying with sodium sulfate. Then, the hexane was concentrated under reduced pressure. Purification by silica gel chromatography using 4% dichloromethane in hexane gave 2-bromo-5,3′-bis-octyloxy-biphenyl corresponding to the compound III of the reaction scheme 1 (Yield: 6.36 g, 58.1%), R1 and R2 in the formula of the compound III being each independently octyl. The product was identified through the NMR spectrum and element analysis that it had the identical structure with the compound III.

Workup

  1. temperatureAfter cooling to room temperature
  2. distillationdistilled water
  3. additionwas added to the resultant
  4. filtrationby filtering three times with hexane
  5. washwashing three times with distilled water
  6. dry with materialdrying with sodium sulfate
  7. concentrationThen, the hexane was concentrated under reduced pressure
  8. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-6a7e54ee2840405db73e972877a01018
Source dataset
uspto-grants-2005_08
Patent number
US06933063B2

Reaction notes

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