Benzyl Bromide → Ethyl 4-(phenylmethoxy)benzoate

HRID 6585Notes

Reaction equation

HRID 6585 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(CC1C=CC=CC=1)(C1C=CC=CC=1)=O.[OH:24][C:25]1[CH:35]=[CH:34][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:27][CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O.CN(C=O)C>[CH2:1]([O:24][C:25]1[CH:26]=[CH:27][C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[CH:34][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8434EthylparabenHCID 99482-PhenylacetophenoneHCID 10796Cesium carbonate

Product 1

HCID 191414Ethyl 4-(phenylmethoxy)benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

35 mmol of benzyl bromide (BzBn, 35 mmol of ethyl 4-hydroxybenzoate (10), 14 g of Cs2CO3 and 40 ml of DMF were combined and stirred at RT ove night. Then the reaction mixture was poured into water and the product was collected by extraction. The organic solution was washed with brine and dried over MgSO4. After evaporation of solvent, pure product was obtained in yield of 100%.

Workup

  1. customthe product was collected by extraction
  2. washThe organic solution was washed with brine
  3. dry with materialdried over MgSO4
  4. customAfter evaporation of solvent
  5. custompure product was obtained in yield of 100%

Sources & evidence

ORD record
ord-424348839da04f94a84ae091f5ab15fa
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Reaction notes

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