Methyl iodide → 2-(4-Fluorophenyl)propionic acid

HRID 476229

Reaktionsgleichung

Reaktionsgleichung von HRID 476229
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11]C)=[O:10])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:15]I>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:15])[C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2733233Methyl 2-(4-fluorophenyl)acetate

Produkt 1

HCID 27239152-(4-Fluorophenyl)propionic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Methyl (4-fluorophenyl)acetate (0.5 g) was dissolved in DMF (81 mL). The mixture was cooled in an ice bath and NaH (131 mg, 60% w/w in mineral oil) was added. The mixture was stirred for 1 h at RT and again cooled in an ice bath before the addition of MeI (633 mg). The mixture was warmed to RT and, the reaction was quenched with ½ (sat.) aqueous ammonium chloride. Work up consisted of extraction of the aqueous layer with ether (2×). The combined organic fractions were washed with water and brine, then dried (MgSO4). The solvent was evaporated under reduced pressure and methyl 2-(4-fluorophenyl)propanoate was purified on silica gel (ethyl acetate/hexanes). Methyl 2-(4-fluorophenyl)propanoate (420 mg) was dissolved in 12 mL THF and 6 mL MeOH. 6 mL of KOH (2M) was added and the mixture was stirred for 2 h at RT. Water was added and the organic solvents were removed. The base was quenched with icy hydrochloric acid (1N), DCM was added and the phases separated with a phase separator. The solvent was removed under reduced pressure to provide the title compound.

Aufarbeitung

  1. temperatureThe mixture was cooled in an ice bath
  2. temperatureThe mixture was warmed to RT
  3. customthe reaction was quenched with ½ (sat.) aqueous ammonium chloride
  4. extractionWork up consisted of extraction of the aqueous layer with ether (2×)
  5. washThe combined organic fractions were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated under reduced pressure and methyl 2-(4-fluorophenyl)propanoate
  8. customwas purified on silica gel (ethyl acetate/hexanes)
  9. dissolutionMethyl 2-(4-fluorophenyl)propanoate (420 mg) was dissolved in 12 mL THF
  10. addition6 mL of KOH (2M) was added
  11. stirringthe mixture was stirred for 2 h at RT
  12. additionWater was added
  13. customthe organic solvents were removed
  14. customThe base was quenched with icy hydrochloric acid (1N), DCM
  15. additionwas added
  16. customthe phases separated with a phase separator
  17. customThe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ae9b34233cb44bc3968b5409f2738b4f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637671B2

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