Benzyl Bromide → HCID 14888726, compound

HRID 487812Notes

Reaction equation

HRID 487812 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. customwas 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-e826a4bfbfa44ed1b5336a1ebfdad4f4
Source dataset
uspto-grants-1994_03
Patent number
US05296608

Reaction notes

Loading…