Benzyl Bromide → HCID 14888726, compound

HRID 1721242Notes

Reaction equation

HRID 1721242 reaction equation
[C:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11](C)[C:12]([O:14][C:15]([CH3:18])(C)C)=[O:13])=[CH:7][CH:6]=1)(O)=O.[C:20](=[O:23])([O-])[O-:21].[K+].[K+].C(Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29]C=1>CN(C=O)C>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][C:8]1[CH:7]=[CH:6][C:5]([CH2:4][CH2:1][C:20]([O:21][C:5]([CH3:10])([CH3:6])[CH3:4])=[O:23])=[CH:10][CH:9]=1)[C:18]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:27]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 22417274HCID 22417274, compound

Product 1

HCID 14888726HCID 14888726, compoundYield 184%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 1,1-dimethylethyl 4-(carboxymethyl)phenylpropanoate (5.3 g, 20.0 mmol) and potassium carbonate (2.8 g, 20.0 mmol) in DMF (30 mL) was added benzyl bromide (3.42 g, 20 mmol). After stirring for 24 h, the solvent was removed in vacuo and the residue was extracted with hexanes (100 mL). Filtration and removal of the solvent under reduced pressure gave 1,1-dimethylethyl 3-[4-(2-benzyloxy-2-oxo-ethyl)phenyl]propanoate (6.5 g, 18.4 mmol) as a colorless liquid in 92% yield.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionthe residue was extracted with hexanes (100 mL)
  3. filtrationFiltration and removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-4713d0e241cd4c0fb32de5140b4a7c10
Source dataset
uspto-grants-1996_04
Patent number
US05508437

Reaction notes

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