Methanol → Methyl 2-(4-cyano-2,5-difluorophenyl)acetate
Reaktionsgleichung
[C:1]([C:3]1[C:8]([F:9])=[CH:7][C:6]([CH2:10][C:11]([OH:13])=[O:12])=[C:5]([F:14])[CH:4]=1)#[N:2].S(Cl)(Cl)=O.[CH3:19]O>>[CH3:19][O:12][C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[C:8]([F:9])[C:3]([C:1]#[N:2])=[CH:4][C:5]=1[F:14]Komponenten
4
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
(4-Cyano-2,5-difluorophenyl)acetic acid (0.5 g, 2.5 mmol) was dissolved in methanol (20 mL), and thionyl chloride (0.5 mL) was added drop wise to the solution. The reaction was heated to 85° C. for 4 hours. Then it was cooled and evaporated to dryness in vacuo. The residue was partitioned between ethyl acetate and saturated NaHCO3. The organic layer was dried over MgSO4, filtered, and the filtrate was evaporated to dryness under reduced pressure to yield the title compound after purification on silica gel (eluted with 5-20% ethyl acetate-hexanes) as an off white solid. 1H NMR (500 MHz, CDCl3): δ 7.31 (dd, J=5.2, J=5.2 Hz, 1H), 7.19 (dd, J=5.7, J=5.8 Hz, 1H), 3.73 (s, 3H), 3.71 (s, 2H). LC-MS (IE, m/z): 212 [M+1]+.