4-Iodophenol → 4-Fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester

HRID 1665240Notes

Reaction equation

HRID 1665240 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH2:11]Br)[CH:5]=1.[I:14][C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[C:6]([CH2:11][O:21][C:18]2[CH:19]=[CH:20][C:15]([I:14])=[CH:16][CH:17]=2)[CH:5]=1

Participants

5

Reactant 3

HCID 108944-IodophenolHCID 11430Potassium CarbonateHCID 53419607Benzoic acid, 3-(bromomethyl)-4-fluoro-, methyl ester

Product 1

HCID 671503534-Fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl esterYield 74.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Bromomethyl-4-fluorobenzoic acid methyl ester (3.0 g, 12.1 mmol) was mixed with 4-iodophenol (3.2 g, 14.6 mmol) in acetone (75 mL) containing dry potassium carbonate (2.5 g, 18 mmol). The mixture was refluxed for 6 hrs and then filtered. The filtrate was concentrated and extracted with ether and water. The organic layer was dried over sodium sulfate and solvents were evaporated. The residue was purified through flash column chromatography (120 g silica gel, 0% to 20% ethyl acetate in hexanes over 40 minutes) to give clear oil as 4-fluoro-3-(4-iodophenoxy)methylbenzoic acid methyl ester (3.48 g, 74.4%).

Workup

  1. temperatureThe mixture was refluxed for 6 hrs
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated
  4. extractionextracted with ether and water
  5. dry with materialThe organic layer was dried over sodium sulfate and solvents
  6. customwere evaporated
  7. customThe residue was purified through flash column chromatography (120 g silica gel, 0% to 20% ethyl acetate in hexanes over 40 minutes)

Sources & evidence

ORD record
ord-dc31e9fad0954bdd9855b18550548ea6
Source dataset
uspto-grants-2011_10
Patent number
US08039495B2

Reaction notes

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