Diethyl Ether → 1-Cyclopropyl-2-(2-fluorophenyl)ethan-1-one

To a suspension of magnesium powder (7.2 g) in anhydrous diethyl ether (60 ml) was added a solution of 2-fluorobenzylbromide (30 ml) in diethyl ether (30 ml), then the mixture was stirred at room temperature for 1 hour. The reaction mixture was added dropwise to a solution of cyclopropyl cyanide (18.2 ml) in diethyl ether (120 ml) over 100 minutes. After stirring for 30 minutes at room temperature the stirred mixture was heated under reflux for 1 hour. After the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution. The ethyl acetate layer was washed successively with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and then evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column using toluene as the eluant to afford the desired product (23 g containing solvent) as a yellow liquid.

1. stirringAfter stirring for 30 minutes at room temperature the stirred mixture
2. temperaturewas heated
3. temperatureunder reflux for 1 hour
4. customAfter the reaction
5. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous ammonium chloride solution
6. washThe ethyl acetate layer was washed successively with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. customevaporated under reduced pressure
9. customThe residue was purified by chromatography on a silica gel column

ORD record

ord-d53bfb4cffaf4cdf8aab8bfa3201d086

Source dataset

uspto-grants-2004_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06693115B2