Hydrochloric Acid → 1-(4-Bromophenyl)cyclopropane-1-carboxylic acid

Temperature

100 °C

A solution of 4-bromophenylacetonitrile (50.0 g, 255 mmol), 1-bromo-2-chloroethane (26.5 mL, 319 mmol), benzyltriethylammonium chloride (1.16 g, 5.10 mol), and potassium hydroxide (100 g, 1.79 mol) in water (100 mL) was stirred at 50° C. for 3 h. Ethanol (400 mL) was added to the reaction mixture, and the mixture was stirred at 100° C. for 3 days. The reaction mixture was neutralized by pouring it into 5 N hydrochloric acid (360 mL) with ice cooling. The reaction mixture was extracted with dichloromethane, the organic layer was dried with anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue, and the precipitate was collected by filtration and dried under reduced pressure to obtain the title compound (50.4 g, 82%) as a white solid.

1. extractionThe reaction mixture was extracted with dichloromethane
2. dry with materialthe organic layer was dried with anhydrous sodium sulfate
3. distillationthe solvent was distilled off under reduced pressure
4. additionDiisopropyl ether was added to the residue
5. filtrationthe precipitate was collected by filtration
6. customdried under reduced pressure

ORD record

ord-5f408d16256b4a419c52d9fee5dde610

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927536B2