反応 #2028870

反応方程式

acetyl chloride

Aluminum chloride

2-fluoroanisole

→

material

収率 92.0%

3′-fluoro-4′-methoxyacetophenone

収率 92.0%

溶媒

chloroform

反応条件

後処理

1. 1
   その他fitted with a mechanical stirrer
2. 2
   温度cooled by means of an ice bath
3. 3
   温度maintaining the temperature between 5°-10° C
4. 4
   その他The resultant layers were separated
5. 5
   抽出the aqueous layer was extracted with dichloromethane (2×250 mL)
6. 6
   洗浄The combined organic layers were washed with water (2×150 mL)
7. 7
   乾燥dried over anhydrous MgSO4
8. 8
   ろ過filtered
9. 9
   濃縮concentrated in vacuo to a volume of 300 mL
10. 10
    workup.ADDITIONHexanes were added
11. 11
    その他a white solid formed which
12. 12
    その他was isolated by filtration and air
13. 13
    その他dried
14. 14
    その他This material was recrystallized from a mixture of dichloromethane and hexanes

実験手順

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).

出典