Réaction #2028870

Équation de réaction

acetyl chloride

Aluminum chloride

2-fluoroanisole

→

material

Rendement 92.0%

3′-fluoro-4′-methoxyacetophenone

Rendement 92.0%

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   Autrefitted with a mechanical stirrer
2. 2
   Températurecooled by means of an ice bath
3. 3
   Températuremaintaining the temperature between 5°-10° C
4. 4
   AutreThe resultant layers were separated
5. 5
   Extractionthe aqueous layer was extracted with dichloromethane (2×250 mL)
6. 6
   LavageThe combined organic layers were washed with water (2×150 mL)
7. 7
   Séchagedried over anhydrous MgSO4
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated in vacuo to a volume of 300 mL
10. 10
    workup.ADDITIONHexanes were added
11. 11
    Autrea white solid formed which
12. 12
    Autrewas isolated by filtration and air
13. 13
    Autredried
14. 14
    AutreThis material was recrystallized from a mixture of dichloromethane and hexanes

Mode opératoire

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).

Source