Reaktion #2028870

Reaktionsgleichung

acetyl chloride

Aluminum chloride

2-fluoroanisole

→

material

Ausbeute 92.0%

3′-fluoro-4′-methoxyacetophenone

Ausbeute 92.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigefitted with a mechanical stirrer
2. 2
   Temperaturcooled by means of an ice bath
3. 3
   Temperaturmaintaining the temperature between 5°-10° C
4. 4
   SonstigeThe resultant layers were separated
5. 5
   Extraktionthe aqueous layer was extracted with dichloromethane (2×250 mL)
6. 6
   WaschenThe combined organic layers were washed with water (2×150 mL)
7. 7
   Trocknendried over anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated in vacuo to a volume of 300 mL
10. 10
    workup.ADDITIONHexanes were added
11. 11
    Sonstigea white solid formed which
12. 12
    Sonstigewas isolated by filtration and air
13. 13
    Sonstigedried
14. 14
    SonstigeThis material was recrystallized from a mixture of dichloromethane and hexanes

Vorschrift

Aluminum chloride, (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution acetyl chloride (51.0 g, 0.65 mol) was added dropwise, maintaining the temperature between 5°-10° C. The mixture was stirred for 10 minutes at 5° C. before the dropwise addition at 5°-10° C. of 2-fluoroanisole (62.6 g, 0.5 mol). The mixture was stirred at 0°-10° C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with dichloromethane (2×250 mL). The combined organic layers were washed with water (2×150 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo to a volume of 300 mL. Hexanes were added and a white solid formed which was isolated by filtration and air dried. This material was recrystallized from a mixture of dichloromethane and hexanes to afford (77.2 g, 92%) of material suitable for use in the next step: mp 92°-94° C.; 1H NMR (DMSO-d6) 7.8 (m, 2H), 7.3 (t, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

Quelle