Benzyl Bromide → 1-(2,4-Bis(benzyloxy)-5-chlorophenyl)ethanone

HRID 389924Notes

Reaction equation

HRID 389924 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:9][C:10]1[C:11]([OH:20])=[CH:12][C:13]([OH:19])=[C:14]([C:16](=[O:18])[CH3:17])[CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([O:19][C:13]1[CH:12]=[C:11]([O:20][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]([Cl:9])=[CH:15][C:14]=1[C:16](=[O:18])[CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 172451191-(5-Chloro-2,4-dihydroxyphenyl)ethan-1-one

Product 1

HCID 179636911-(2,4-Bis(benzyloxy)-5-chlorophenyl)ethanoneYield 94.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (17.5 ml, 0.147 mol) was added to a mixture of 1-(5-chloro-2,4-dihydroxyphenyl)ethanone (11 g, 0.059 mol) and potassium carbonate (20.34 g, 0.147 mol) in acetonitrile (180 ml). The mixture was stirred at reflux for 6 h and then allowed to cool to RT and stirred overnight. The mixture was filtered, and the solid residue was rinsed with DCM (3×50 ml). The combined organic filtrates were evaporated under vacuo to give a pale yellow solid. The latter was triturated with a mixture of hexane/EtOAc (175/7.5) and filtered to afford the title compound 1-[2,4-bis(benzyloxy)-5-chlorophenyl]ethanone (20.4 g, 93% yield) as an off-white solid.

Workup

  1. temperatureat reflux for 6 h
  2. stirringstirred overnight
  3. filtrationThe mixture was filtered
  4. washthe solid residue was rinsed with DCM (3×50 ml)
  5. customThe combined organic filtrates were evaporated under vacuo
  6. customto give a pale yellow solid
  7. customThe latter was triturated with a mixture of hexane/EtOAc (175/7.5)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-e447a01e8b624cfab41f508a4209a358
Source dataset
uspto-grants-2013_02
Patent number
US08383616B2

Reaction notes

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