1-Bromo-3-chloropropane → 5-Chloro-2-(4-chlorophenyl)-2-methylpentanoic acid

Temperature

-20 °C

Under a nitrogen atmosphere, to a mixture of 2-(4-chlorophenyl)propanoic acid (13.3 g) in THF (140 mL) was added n-butyllithium (1.6M hexane solution, 90.3 mL) at −60° C. to —70° C., and the mixture was allowed to warm to −20° C. 1-Bromo-3-chloropropane (11.4 g) was added to the reaction mixture at −20° C. to 10° C., and the mixture was stirred at room temperature for 12 hr. The reaction mixture was extracted with 1N aqueous sodium hydroxide solution (2×100 mL), and the extract was acidified with 3N hydrochloric acid (100 mL). The mixture was extracted with ethyl acetate (3×100 mL), the extract was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (15.7 g).

1. extractionThe reaction mixture was extracted with 1N aqueous sodium hydroxide solution (2×100 mL)
2. extractionThe mixture was extracted with ethyl acetate (3×100 mL)
3. dry with materialthe extract was dried over magnesium sulfate
4. customthe solvent was evaporated under reduced pressure
5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

ORD record

ord-2b6c2be79119446f96e5a7de3d87f52f

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822699B2