Phenol → HCID 13266144, compound

HRID 418560Notes

Reaction equation

HRID 418560 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=CC=1.[C:8]([O-])([O-])=O.[K+].[K+].[CH2:14]([Br:21])[C:15]1[CH:20]=CC=CC=1.[C:22]([O:25][CH2:26][CH3:27])(=O)[CH3:23]>CN(C=O)C.O>[Br:21][C:14]1[CH:15]=[CH:20][C:22]([O:25][C:26]2[CH:27]=[CH:4][CH:5]=[CH:6][C:1]=2[OH:7])=[CH:23][CH:8]=1

Participants

7

Reactant 4

HCID 996PhenolHCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium Carbonate

Product 1

HCID 13266144HCID 13266144, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(4-Bromophenoxy)-phenol was prepared by reported method. A mixture of phenol (2.65 g, 10.0 mmol) and K2CO3 (1.45 g, 10.5 mmol) in DMF (20 mL) was stirred for 0.5 hours, and then benzylbromide (1.56 mL, m 13.0 mmol) was added. The reaction mixture was stirred at room temperature for 3 hours, then was diluted with ethyl acetate and water. The layers were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, 2 N HCl, sat'd NaHCO3, and brine, dried under anhydrous MgSO4, filtered, and dried under reduced pressure. The residue was purified by column chromatography to give the desired product as a white solid (3.00 g, 84%). 1H NMR (500 MHz, CDCl3) δ 5.06-5.13 (m, 2H), 6.85 (d, J=9.0 Hz, 2H), 7.00 (t, J=9.0 Hz, 1H), 7.05-7.23 (m, 5H), 7.26-7.37 (m, 3H), 7.42 (d, J=9.0 Hz, 2H); 13C NMR (126 MHz, CDCl3) δ 70.6, 114.6, 115.3, 118.6, 121.9, 122.4, 125.7, 127.2, 128.0, 128.6, 132.5, 136.8, 144.9, 150.7, 157.9;

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 3 hours
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water, 2 N HCl
  5. customdried under anhydrous MgSO4
  6. filtrationfiltered
  7. customdried under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-1d3380fcaf4e49d890cdaeb0e70dc604
Source dataset
uspto-grants-2012_01
Patent number
US08093287B2

Reaction notes

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