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

HRID 1891136Notes

Reaction equation

HRID 1891136 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 90%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzyl bromide (30 mL) was added to a mixture of 1-(5-chloro-2,4-dihydroxy-phenyl)-ethanone (20 g, 0.107 moles) and potassium carbonate (37 g, 2.5 equiv) in acetonitrile (350 mL). The mixture was heated at reflux for 6 hours then allowed to cool and stirred overnight. The mixture was filtered and the solids were washed with dichloromethane (3×100 mL). The combined organic extracts were evaporated in vacuo to leave a pale yellow solid which was triturated with a mixture of hexane (350 mL)/ethyl acetate (15 mL) and filtered to give an off-white solid, 1-(2,4-bis-benzyloxy-5-chloro-phenyl)-ethanone (35.4 g, 90%). 1H NMR (400 MHz) consistent with structure.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 hours
  3. temperatureto cool
  4. filtrationThe mixture was filtered
  5. washthe solids were washed with dichloromethane (3×100 mL)
  6. customThe combined organic extracts were evaporated in vacuo
  7. customto leave a pale yellow solid which
  8. customwas triturated with a mixture of hexane (350 mL)/ethyl acetate (15 mL)
  9. filtrationfiltered

Sources & evidence

ORD record
ord-433cd2e7c77c4bdb852732995598867e
Source dataset
uspto-grants-2013_08
Patent number
US08507480B2

Reaction notes

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