5-Bromo-2-chlorobenzoyl chloride → (5-Bromo-2-chloro-phenyl)-(2,3-difluoro-4-methoxy-phenyl)methanone

Temperature

0 °C

To a solution of 5-bromo-2-chlorobenzoyl chloride 21d (3.4 g, 13.4 mmol) and 1,2-difluoro-3-methoxybenzene 21b (2.4 g, 16.7 mmol) in dichloromethane (40 mL) was added anhydrous aluminium chloride (1.82 g, 13 mmol) at 0° C. The mixture was stirred at 0° C. for 16 hours. Then the reaction mixture was quenched with hydrochloric acid (4 mL, 2 M) and warmed up to room temperature. The mixture was extracted with dichloromethane (40 mL×4). The combined organic layers were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to give the title compound 21e as yellow liquid (5.4 g, 96.4%). This material was not further purified.

1. customThen the reaction mixture was quenched with hydrochloric acid (4 mL, 2 M)
2. temperaturewarmed up to room temperature
3. extractionThe mixture was extracted with dichloromethane (40 mL×4)
4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo

ORD record

ord-935e289b33e64f96ac2b6a4d5488c475

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09394329B2