Potassium Carbonate → HCID 69206618, compound

HRID 2374115Notes

Reaction equation

HRID 2374115 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[CH:10][CH:9]=1.Cl[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CC(=O)CC.[I-].[K+]>[Br:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 950934-Bromo-4'-hydroxybiphenylHCID 86215670HCID 86215670, compound

Product 1

HCID 69206618HCID 69206618, compound

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

Potassium carbonate (0.56 g, 4.8 mmol) was added to a solution of 4-bromo-4′-hydroxybiphenyl (0.80 g, 3.2 mmol) in butanone (50 ml) with potassium iodide (0.1 g) as catalyst. This mixture was left stirring at room temperature for 10 min and a solution of 1-chloro-7,7-dimethyloctance from step 6 (0.50 g, 2.8 mmol) in butanone (10 ml) was added dropwise. The reaction mixture was heated under reflux for 44 h. The mixture was filtered and butanone was removed from the filtrate under reduced pressure. The product was extracted into ether (2×75 ml) and the combined ethereal extracts were washed successively with water, 5% sodium hydroxide and water, and dried (MgSO4). The solvent was removed in vacuo and the residue was purified by column chromatography [DCM] to give a white powder.

Workup

  1. waitThis mixture was left
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 44 h
  4. filtrationThe mixture was filtered
  5. custombutanone was removed from the filtrate under reduced pressure
  6. extractionThe product was extracted into ether (2×75 ml)
  7. washthe combined ethereal extracts were washed successively with water, 5% sodium hydroxide and water
  8. dry with materialdried (MgSO4)
  9. customThe solvent was removed in vacuo
  10. customthe residue was purified by column chromatography [DCM]
  11. customto give a white powder

Sources & evidence

ORD record
ord-1bcbbfbb672443d0b6d94cefb0d937bd
Source dataset
uspto-grants-2008_12
Patent number
US07462427B2

Reaction notes

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