반응 #2028870

반응 방정식

acetyl chloride

Aluminum chloride

2-fluoroanisole

→

material

수율 92.0%

3′-fluoro-4′-methoxyacetophenone

수율 92.0%

용매

chloroform

반응 조건

후처리

1. 1
   기타fitted with a mechanical stirrer
2. 2
   온도cooled by means of an ice bath
3. 3
   온도maintaining the temperature between 5°-10° C
4. 4
   기타The resultant layers were separated
5. 5
   추출the aqueous layer was extracted with dichloromethane (2×250 mL)
6. 6
   세척The combined organic layers were washed with water (2×150 mL)
7. 7
   건조dried over anhydrous MgSO4
8. 8
   여과filtered
9. 9
   농축concentrated in vacuo to a volume of 300 mL
10. 10
    workup.ADDITIONHexanes were added
11. 11
    기타a white solid formed which
12. 12
    기타was isolated by filtration and air
13. 13
    기타dried
14. 14
    기타This material was recrystallized from a mixture of dichloromethane and hexanes

실험 절차

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).

출처