Benzyl Bromide → HCID 86047407, compound

HRID 2220644Notes

Reaction equation

HRID 2220644 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:27]([O:26][C:24](=[O:25])[CH2:23][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([O:9][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:11][CH:12]=2)=[CH:17][CH:18]=1)[CH3:28]

Participants

5

Reactant 3

HCID 7498Benzyl Bromide3×HCID 11430Potassium CarbonateHCID 44236644HCID 44236644, compound

Product 1

HCID 86047407HCID 86047407, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl bromide (0.23 mL) was added to a mixture of ethyl (4′-hydroxybiphenyl-4-yloxy)acetate (0.50 g) and potassium carbonate (0.38 g) in N,N-dimethylformamide (5 mL) at room temperature with stirring, and the mixture was stirred at that temperature for 1 hr. Benzyl bromide (0.021 mL) was added to the reaction mixture. After being stirred for 30 minutes, benzyl bromide (0.044 mL) was added, and the mixture was stirred for 30 minutes. The reaction mixture was partitioned between methylene chloride and water, and the aqueous layer was extracted with methylene chloride. The combined organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3-1/2-2/1) to afford the title compound (0.64 g).

Workup

  1. stirringthe mixture was stirred at that temperature for 1 hr
  2. stirringAfter being stirred for 30 minutes
  3. stirringthe mixture was stirred for 30 minutes
  4. customThe reaction mixture was partitioned between methylene chloride and water
  5. extractionthe aqueous layer was extracted with methylene chloride
  6. washThe combined organic layer was washed with water and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/3-1/2-2/1)

Sources & evidence

ORD record
ord-4c45516814f1473aa04abe612d18b16e
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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