Potassium Carbonate → 4-Iodo-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl Ester

HRID 1475741Notes

Reaction equation

HRID 1475741 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+]>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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5706841-(2-Bromoethyl)-3-methylbenzeneHCID 10378812Methyl 3-hydroxy-4-iodobenzoate

Product 1

HCID 671709004-Iodo-3-(2-m-tolyl-ethoxy)-benzoic Acid Methyl EsterYield 32.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.0 g of 3-hydroxy-4-iodo-benzoic acid methyl ester, 7.2 g of 1-(2-bromo-ethyl)-3-methyl-benzene and 10.0 g of potassium carbonate were stirred in 100 ml of anhydrous DMF for 28 h at 80° C. The solvent was evaporated and the residue dissolved in 200 ml of water and 400 ml of EA. The organic layer was separated, washed with 200 ml of water, dried with magnesium sulfate and evaporated. Silica gel chromatography (EA/HEP gradient) of the residue yielded 4.66 g of the title compound.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in 200 ml of water
  3. customThe organic layer was separated
  4. washwashed with 200 ml of water
  5. dry with materialdried with magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-d08fd08a6fc941918d33decc6c1c6bd3
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

Loading…