Methanol → Methyl 2-(4-chloro-2-fluorophenyl)acetate

Reaktionsgleichung

S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([OH:15])=[O:14])=[C:8]([F:16])[CH:7]=1.[CH3:17]O>>[CH3:17][O:14][C:13](=[O:15])[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([Cl:5])=[CH:7][C:8]=1[F:16]

Komponenten

Edukt 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 2757563(4-Chloro-2-fluorophenyl)acetic acid

Produkt 1

HCID 57443493Methyl 2-(4-chloro-2-fluorophenyl)acetateAusbeute 96 %

Versuchsvorschrift

Thionyl chloride (0.94 mL, 0.0129 mol) was added dropwise to a solution of (4-chloro-2-fluoro-phenyl)acetic acid (2.03 g, 0.0108 mol) in methanol (100 mL) at 0° C., and the mixture was stirred at room temperature overnight. The solvent was distilled off under reduced pressure. The resulting residue was subjected to silica gel chromatography (n-hexane/ethyl acetate=1/0 to 3/1) to give the title compound (2.11 g, 96%).