Benzyl Bromide → HCID 14888726, compound

HRID 1647067Notes

Reaction equation

HRID 1647067 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-d56e61d6b540415bb3ca1217d3b6d50e
Source dataset
uspto-grants-1993_01
Patent number
US05182263

Reaction notes

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