Methyl iodide → 2-(2-Fluoro-4-methoxyphenyl)-2-propanol

HRID 1252797Notes

Reaction equation

HRID 1252797 reaction equation
[CH3:1]I.[Mg].[CH3:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[F:15])=[O:6].[NH4+].[Cl-]>C(OCC)C>[F:15][C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[C:5]([OH:6])([CH3:1])[CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5928212'-Fluoro-4'-methoxyacetophenoneHCID 5462224Magnesium

Product 1

HCID 134938442-(2-Fluoro-4-methoxyphenyl)-2-propanolYield 80.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

17.75 g (0.125 mole) methyliodide are dissolved in diethylether and the resulting solution is added dropwise with stirring to 3.04 g magnesium chips in 15 ml anhydrous ether. The mixture is then heated under reflux for 30 minutes, followed by the dropwise addition with stirring of a solution of 16.82 g (0.1 mole) 2-fluoro-4-methoxy-acetophenone in diethylether. After heating under reflux for 2 hours, the reaction mixture is cooled, poured onto ice and the corresponding deposit dissolved by addition of aqueous NH4Cl solution. The ether phase is separated off, the aqueous phase is extracted with ether, the combined ether phases are washed with aqueous solutions of NaHSO3, NaHCO3 and then with pure water, dried over Na2SO4 and the ether removed. Distillation of the residual oil in a high vacuum gives 14.9 g 2-(2-fluoro-4-methoxyphenyl)-2-propanol.

Workup

  1. additionthe resulting solution is added dropwise
  2. temperatureThe mixture is then heated
  3. temperatureunder reflux for 30 minutes
  4. additionfollowed by the dropwise addition
  5. temperatureAfter heating
  6. temperatureunder reflux for 2 hours
  7. temperaturethe reaction mixture is cooled
  8. additionpoured onto ice
  9. customThe ether phase is separated off
  10. extractionthe aqueous phase is extracted with ether
  11. washthe combined ether phases are washed with aqueous solutions of NaHSO3, NaHCO3
  12. dry with materialwith pure water, dried over Na2SO4
  13. customthe ether removed
  14. distillationDistillation of the residual oil in a high vacuum

Sources & evidence

ORD record
ord-5b92d93daf3f4b858717dc80c624a6c3
Source dataset
uspto-grants-1988_05
Patent number
US04745233

Reaction notes

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