Anisole → (5-Bromo-2-fluoro-phenyl)-(4-methoxy-phenyl)-methanone

Temperature

0 °C

To a solution of 5-bromo-2-fluoro-benzoyl chloride (27.0 g, 114 mmol) and anisole (12.9 g, 13.0 mL, 119 mmol) in dichloromethane (150 mL) at 0° C. was added aluminum trichloride (16.2 g, 119 mmol) portionwise so that the internal temperature remained below 10° C. After stirring for 4 hours at 0° C., the solution was poured over crushed ice and the resulting mixture was stirred. After 30 minutes, the organic phase was removed and the aqueous phase was extracted two times with dichloromethane. The combined organic phases were washed once with aqueous 1M hydrochloric acid solution, once with aqueous 1M sodium hydroxide solution, and once with brine. The organic phase was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was recrystallized from ethanol to afford (5-bromo-2-fluoro-phenyl)-(4-methoxy-phenyl)-methanone (22.5 g, 64%) as a white solid.

1. customremained below 10° C
2. additionthe solution was poured
3. customover crushed ice
4. stirringthe resulting mixture was stirred
5. waitAfter 30 minutes
6. customthe organic phase was removed
7. extractionthe aqueous phase was extracted two times with dichloromethane
8. washThe combined organic phases were washed once with aqueous 1M hydrochloric acid solution, once with aqueous 1M sodium hydroxide solution
9. dry with materialThe organic phase was dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe resulting residue was recrystallized from ethanol

ORD record

ord-e74f4d26bc5b4e5689960509010aec5f

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080580B2