Реакция #2028870

Уравнение реакции

acetyl chloride

Aluminum chloride

2-fluoroanisole

→

material

Выход 92.0%

3′-fluoro-4′-methoxyacetophenone

Выход 92.0%

Растворители

chloroform

Условия реакции

Обработка

1. 1
   Другоеfitted with a mechanical stirrer
2. 2
   Температураcooled by means of an ice bath
3. 3
   Температураmaintaining the temperature between 5°-10° C
4. 4
   ДругоеThe resultant layers were separated
5. 5
   Экстракцияthe aqueous layer was extracted with dichloromethane (2×250 mL)
6. 6
   ПромывкаThe combined organic layers were washed with water (2×150 mL)
7. 7
   Сушкаdried over anhydrous MgSO4
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated in vacuo to a volume of 300 mL
10. 10
    workup.ADDITIONHexanes were added
11. 11
    Другоеa white solid formed which
12. 12
    Другоеwas isolated by filtration and air
13. 13
    Другоеdried
14. 14
    ДругоеThis material was recrystallized from a mixture of dichloromethane and hexanes

Методика

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).

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