Ethyl Acetate → Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-iodobenzoate

HRID 1623731Notes

Reaction equation

HRID 1623731 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CC(C)=O>[F:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][O:1][C:2]2[CH:11]=[CH:10][C:9]([I:12])=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 680214-Fluorobenzyl bromideHCID 248910Methyl 5-Iodosalicylate

Product 1

HCID 67106887Methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-iodobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of methyl 2-hydroxy-5-iodobenzoate (15 g, 53.9 mmol) in acetone (200 ml) was added 1-(bromomethyl)-4-fluorobenzene (9.95 ml, 81 mmol), potassium carbonate (14.91 g, 108 mmol) and the mixture was refluxed overnight. The mixture was allowed to cool and then filtered to remove the potassium carbonate. The solid potassium carbonate was washed with acetone (100 ml). The organics were combined and evaporated under reduced pressure on a buchi to give a solid. The solid was taken up into ethyl acetate (500 ml) and the organic phase was washed with water (2×200 ml), dried (MgSO4) and evaporated under reduced pressure on a buchi. The solid obtained was recrystallised from cyclohexane to yield the title compound as a white solid. 18.2 g.

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureto cool
  3. filtrationfiltered
  4. customto remove the potassium carbonate
  5. washThe solid potassium carbonate was washed with acetone (100 ml)
  6. customevaporated under reduced pressure on a buchi
  7. customto give a solid
  8. washthe organic phase was washed with water (2×200 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated under reduced pressure on a buchi
  11. customThe solid obtained
  12. customwas recrystallised from cyclohexane

Sources & evidence

ORD record
ord-ef0325114daf425f8ac79e4832193048
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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