Phenol → HCID 20291308, compound

HRID 384113Notes

Reaction equation

HRID 384113 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1.[C:10]1([OH:16])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>O>[O:16]([C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[CH:4][N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 996Phenol3×HCID 11430Potassium Carbonate2×HCID 14512957(2-Bromopyridin-4-yl)methanol

Product 1

HCID 20291308HCID 20291308, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

At 190° C., (2-bromopyridin-4-yl)methanol (550 mg), phenol (330 mg) and potassium carbonate (450 mg) were stirred for 30 minutes. To the reaction solution was added 330 mg of phenol, and the mixture was stirred at the same temperature for further 30 minutes. To the reaction solution were added 700 mg of phenol and 450 mg of potassium carbonate, and the mixture was stirred at the same temperature for further 1 hour. The reaction solution was cooled, then diluted with water, extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-100:0)) to afford the title compound as a brown oil.

Workup

  1. stirringthe mixture was stirred at the same temperature for further 1 hour
  2. temperatureThe reaction solution was cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue obtained
  7. customwas purified by silica gel column chromatography (eluent: ethyl acetate/hexane (0:100-100:0))

Sources & evidence

ORD record
ord-58ebabb87cdb4f8493282d54c05d7858
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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