Bromine → 1-(4-(Benzyloxy)phenyl)-3-phenylpropan-1-one

HRID 446808Notes

Reaction equation

HRID 446808 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrBr>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:17])[CH2:16][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 149668391-(4-(Benzyloxy)phenyl)-3-phenylpropan-1-oneYield 189.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of 1-(4-(benzyloxy)phenyl)ethanone (5.0 g, 0.02 mol) in MeOH (120 mL) was added a solution of Br2 (4.22 g, 0.026 mol) in MeOH (13 mL). The reaction mixture was stirred at RT for 3 h and then concentrated in vacuo. The residue was then treated with HCl (1N, 20 mL), quenched with ice, and the resulting solid precipitate was filtered and dried in vacuo to afford 1-(4-(benzyloxy)phenyl)-3-phenylpropan-1-one (6 g, 89%) as a white solid.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was then treated with HCl (1N, 20 mL)
  3. customquenched with ice
  4. filtrationthe resulting solid precipitate was filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ccfc79540abe44b18e0736d2d3ca1806
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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