Potassium Iodide → Methyl 2-(2-chlorobenzyloxy)-5-fluorobenzoate

HRID 1921865Notes

Reaction equation

HRID 1921865 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[Cl:13][C:14]1[CH:21]=[CH:20][CH:19]=[CH:18][C:15]=1[CH2:16][O:12][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 11905alpha-Bromo-o-chlorotolueneHCID 2783186Methyl 5-fluoro-2-hydroxybenzoate

Product 1

HCID 57864396Methyl 2-(2-chlorobenzyloxy)-5-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

10.0 g (58 mmol) of methyl 5-fluoro-2-hydroxybenzoate [CAS 391-92-4], 13.3 g (64.5 mmol) of 2-chlorobenzyl bromide [CAS 611-17-6], 40.6 g (293 mmol) of potassium carbonate and 14.6 g (88 mmol) of potassium iodide are dissolved in 50 ml of acetone, and stirred under reflux for 12 h. The solvent is distilled out in vacuo, and the residue is taken up in ethyl acetate and washed twice each with 10% strength sodium hydroxide solution, 1 N hydrochloric acid and water. Drying over magnesium sulfate, filtration and washing with ethyl acetate are followed by concentration. The residue is stirred with petroleum ether, and the solid is filtered off with suction and dried on a clay dish. 10.0 g (33.9 mmol, 59% of theory) of the title compound are obtained.

Workup

  1. temperatureunder reflux for 12 h
  2. distillationThe solvent is distilled out in vacuo
  3. washwashed twice each with 10% strength sodium hydroxide solution, 1 N hydrochloric acid and water
  4. dry with materialDrying over magnesium sulfate, filtration
  5. washwashing with ethyl acetate
  6. concentrationare followed by concentration
  7. stirringThe residue is stirred with petroleum ether
  8. filtrationthe solid is filtered off with suction
  9. customdried on a clay dish

Sources & evidence

ORD record
ord-6d04fbf236544bca958220d0ede75cb2
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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