Reacción #2028870

Ecuación de reacción

acetyl chloride

Aluminum chloride

2-fluoroanisole

→

material

Rendimiento 92.0%

3′-fluoro-4′-methoxyacetophenone

Rendimiento 92.0%

Disolventes

chloroform

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrofitted with a mechanical stirrer
2. 2
   Temperaturacooled by means of an ice bath
3. 3
   Temperaturamaintaining the temperature between 5°-10° C
4. 4
   OtroThe resultant layers were separated
5. 5
   Extracciónthe aqueous layer was extracted with dichloromethane (2×250 mL)
6. 6
   LavadoThe combined organic layers were washed with water (2×150 mL)
7. 7
   Secadodried over anhydrous MgSO4
8. 8
   Filtraciónfiltered
9. 9
   Concentraciónconcentrated in vacuo to a volume of 300 mL
10. 10
    workup.ADDITIONHexanes were added
11. 11
    Otroa white solid formed which
12. 12
    Otrowas isolated by filtration and air
13. 13
    Otrodried
14. 14
    OtroThis material was recrystallized from a mixture of dichloromethane and hexanes

Procedimiento

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).

Fuente