Ammonium Chloride → (4-Bromo-2-fluorophenyl)(cyclopropyl)methanone

To magnesium (265 mg), tetrahydrofuran (2 mL) was added, and cyclopropyl bromide (1.1 mL) was added slowly at room temperature, and then the reaction mixture was stirred at room temperature for 1 hour. To a solution of 4-bromo-2-fluorobenzaldehyde (2.0 g) in tetrahydrofuran (20 mL) was added the solution of the obtained Grignard reagent in tetrahydrofuran at 0° C., and then the reaction mixture was stirred at room temperature for 2 days. To the reaction mixture was added a saturated aqueous solution of ammonium chloride, and the reaction mixture was extracted with ethyl acetate. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the titled compound (2.19 g) as a brown oil.

1. stirringthe reaction mixture was stirred at room temperature for 2 days
2. extractionthe reaction mixture was extracted with ethyl acetate
3. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
4. filtrationfiltered
5. concentrationthe filtrate was concentrated under reduced pressure
6. customThe obtained residue was purified by silica gel column chromatography

ORD record

ord-638934eed88f4f0dbc8b24b0878cb74a

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987473B2