Potassium Iodide → Methyl {2-[4-(3,5-difluorophenoxy)phenoxy]ethyl}carbamate

HRID 373786Notes

Reaction equation

HRID 373786 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][O:10][C:11](=[O:16])[NH:12][CH2:13][CH2:14]Cl.[F:17][C:18]1[CH:19]=[C:20]([CH:29]=[C:30]([F:32])[CH:31]=1)[O:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1>CN(C)C=O>[CH3:9][O:10][C:11](=[O:16])[NH:12][CH2:13][CH2:14][O:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][C:20]2[CH:29]=[C:30]([F:32])[CH:31]=[C:18]([F:17])[CH:19]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 251614Methyl (2-chloroethyl)carbamateHCID 133918364-(3,5-Difluorophenoxy)phenol

Product 1

HCID 13502189Methyl {2-[4-(3,5-difluorophenoxy)phenoxy]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21.3 g of potassium carbonate powder, 1.5 g of finely powdered potassium iodide and 16 g of 2-chloroethylcarbamic acid methyl ester are added to a solution of 17.1 g of 4-(3,5-difluorophenoxy)-phenol in 100 ml of dimethylformamide, and the reaction mixture is heated at +95° C. for 15 hours. The reaction mixture is then cooled, poured onto ice-water and extracted repeatedly with ether. The combined ether phases are washed with water and dried over sodium sulfate. The solvent is distilled off completely. The crude product is purified further by chromatography over silica gel (eluant: petroleum ether (40° C.-65° C.)/diethyl ether, 5:1), yielding 2-[4-(3,5-difluorophenoxy)-phenoxy]-ethylcarbamic acid methyl ester, n21D : 1.5394.

Workup

  1. temperaturethe reaction mixture is heated at +95° C. for 15 hours
  2. temperatureThe reaction mixture is then cooled
  3. additionpoured onto ice-water
  4. extractionextracted repeatedly with ether
  5. washThe combined ether phases are washed with water
  6. dry with materialdried over sodium sulfate
  7. distillationThe solvent is distilled off completely
  8. customThe crude product is purified further by chromatography over silica gel (eluant: petroleum ether (40° C.-65° C.)/diethyl ether, 5:1)

Sources & evidence

ORD record
ord-20e9f01896e3477e900d192ee018ec73
Source dataset
uspto-grants-1992_11
Patent number
US05166153

Reaction notes

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