Ethyl Acetate → 4-Iodo-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl Ester

HRID 1918389Notes

Reaction equation

HRID 1918389 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([OH:11])[CH:5]=1.Br[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[CH:17]=1.C([O-])([O-])=O.[K+].[K+].CC(=O)OCC>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([I:10])=[C:6]([O:11][CH2:14][CH2:15][C:16]2[CH:17]=[C:18]([CH3:22])[CH:19]=[CH:20][CH:21]=2)[CH:5]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium Carbonate2×HCID 5706841-(2-Bromoethyl)-3-methylbenzene2×HCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 671709004-Iodo-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl EsterYield 80.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g of 3-Hydroxy-4-iodo-benzoic acid methyl ester, 14.3 g of 1-(2-bromo-ethyl)-3-methyl-benzene, and 10.0 g of K2CO3 were stirred in anhydrous DMF at 80° C. for 10 h. Then, 14.3 g of 1-(2-bromo-ethyl)-3-methyl-benzene, and 10.0 g of K2CO3 were added and stirring was continued at 80° C. for 10 h. 400 ml of EA were then added and the mixture was washed twice using 200 ml of water each. The organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EAIHEP (gradient) yielded 11.5 g of the title compound, colorless oil.

Workup

  1. washthe mixture was washed twice
  2. customThe organic layer was then dried
  3. customevaporated

Sources & evidence

ORD record
ord-e58c8a22c33e40159e29accde599df14
Source dataset
uspto-grants-2013_12
Patent number
US08618304B2

Reaction notes

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