Hydrochloric Acid → 4-Chloro-2-(3,4,5-trifluorophenyl)butyric acid

Temperature

-78 °C

A 2.66 M solution of butyl lithium in hexane (20 mL) was added to a solution of 3,4,5-trifluorophenylacetic acid (5.00 g) in THF (150 mL) in a nitrogen atmosphere at −78° C., and the reaction solution was stirred at −78° C. for 20 minutes. The reaction solution was further stirred at 0° C. for one hour. Then, 1-bromo-2-chloroethane (2.2 mL) was added at 0° C., and the reaction solution was stirred at room temperature for 14 hours. Ethyl acetate and 1 N hydrochloric acid were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with a saturated sodium chloride solution. The resulting organic layer was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 4.54 g of the title compound. The property values of the compound are as follows.

1. stirringThe reaction solution was further stirred at 0° C. for one hour
2. stirringthe reaction solution was stirred at room temperature for 14 hours
3. customthe organic layer was separated
4. washThe resulting organic layer was washed with a saturated sodium chloride solution
5. dry with materialThe resulting organic layer was dried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system)

ORD record

ord-64983c77b644471fa540bac75c1a8a43

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897632B2