Acetyl chloride → 1-(3-Fluoro-4-methoxyphenyl)ethan-1-one

To a solution of 700 ml of dried methylene chloride and 157 g of acetyl chloride was added dropwise 267 g of anhydrous aluminum chloride over 30 minutes with stirring while holding temperature at 15°-25° C., which were further stirred at room temperature for about 2 hours. Separately, a solution of 206 g of o-fluoroanisole and 170 ml of dried methylene chloride was cooled on an ice water bath, to which was added dropwise the previously prepared solution of acetyl chloride and aluminum chloride in methylene chloride over about 2.5 hours. The resulting mixture was further stirred on the ice water bath for 1 hour and at room temperature for 1 hour. The resulting reaction mixture was poured into 1.4 l of ice water and separated into two layers. The extraction with 400 ml of methylene chloride on aqueous layer was repeated two times, and thereafter the organic layers were gathered, washed with water and dried on magnesium sulfate. After magnesium sulfate was filtered off, the filtrate was concentrated and dried to obtain a light brown crystal. This crystal was recrystallized with ethanol to obtain 242 g (yield: 88%) of a white crystal having a melting point of 89.5°-90.0° C.

1. customat 15°-25° C.
2. stirringwhich were further stirred at room temperature for about 2 hours
3. customThe resulting reaction mixture
4. customseparated into two layers
5. extractionThe extraction with 400 ml of methylene chloride on aqueous layer
6. washwashed with water
7. customdried on magnesium sulfate
8. filtrationAfter magnesium sulfate was filtered off
9. concentrationthe filtrate was concentrated
10. customdried
11. customto obtain a light brown crystal
12. customThis crystal was recrystallized with ethanol

ORD record

ord-660a0d1c4e9345b7b1b0604853a4001d

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05098602