Benzoic acid, 4-(bromomethyl)-2-ethoxy-, ethyl ester → Ethyl 2-ethoxy-4-(2-ethoxy-2-oxoethyl)benzoate

HRID 2415505Notes

Reaction equation

HRID 2415505 reaction equation
Br[CH2:2][C:3]1[CH:13]=[CH:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:5]([O:14][CH2:15][CH3:16])[CH:4]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(O)C>[CH2:15]([O:14][C:5]1[CH:4]=[C:3]([CH2:2][C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH:13]=[CH:12][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:16]

Participants

4

Reactant 1

HCID 10589339Benzoic acid, 4-(bromomethyl)-2-ethoxy-, ethyl ester

Product 1

HCID 10378914Ethyl 2-ethoxy-4-(2-ethoxy-2-oxoethyl)benzoateYield 148.6%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture ethyl 4-bromomethyl-2-ethoxy-benzoate (4, 1 gm, 3.5 mmol), dichlorobis-(triphenylphosphine)palladium catalyst (0.1 gm), ethyl alcohol (5 ml) was heated to 50° C. with CO for 6-15 hrs. Catalyst was filtered and solvent was removed to yield the product ethyl 3-ethoxy-4-ethoxycarbonyl-phenylacetate (1, 0.75 gm, 2.6 mmol, 76%).

Workup

  1. filtrationCatalyst was filtered
  2. customsolvent was removed

Sources & evidence

ORD record
ord-15b92db01f8b494a8d5c1270bfee2230
Source dataset
uspto-grants-2004_11
Patent number
US06818786B2

Reaction notes

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