Toluene → Methyl 3-fluoro-4-methylbenzoate

HRID 220768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220768
S(Cl)(Cl)=O.[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[CH:13][C:14]=1[CH3:15])[C:9]([OH:11])=[O:10].[C:16]1(C)C=CC=CC=1>>[CH3:16][O:10][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][C:14]([CH3:15])=[C:6]([F:5])[CH:7]=1

Komponenten

4

Edukt 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 676873-Fluoro-p-toluic acid

Produkt 1

HCID 18973767Methyl 3-fluoro-4-methylbenzoateAusbeute 83 %

Versuchsvorschrift

Thionyl chloride (9.62 g, 81 mmol) was added to a solution of 3-fluoro-4-methylbenzoic acid (5.0 g, 32.4 mmol) in toluene (50 ml). The mixture was stirred at room temperature for 1.5 h and heated at reflux for 3 h. The sol-vent was removed in vacuo and the residue was taken up in methanol (30 ml) and CH2Cl2 (30 ml) and stirred for 18 h. The mixture was evaporated in vacuo and the residue was taken up in EtOAc (50 ml), washed with saturated NaHCO3 solution (3×75 ml), dried and evaporated in vacuo to yield the title compound (4.5 g, 83%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 3 h
  3. customThe sol-vent was removed in vacuo
  4. stirringCH2Cl2 (30 ml) and stirred for 18 h
  5. customThe mixture was evaporated in vacuo
  6. washwashed with saturated NaHCO3 solution (3×75 ml)
  7. customdried
  8. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a92516418eb34081835e188e8b1ab188
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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