Water → (4-Bromo-2-chlorophenyl)acetic acid

Temperature

75 °C

To 4-bromo-2-chlorobenzyl cyanide (383 g) of Reference Example 14 were added water (908 mL), ethanol (6812 mL) and 85% aqueous potassium hydroxide solution (549 g), and the mixture was stirred at an inside temperature of 75° C. for 13 hr. The mixture was concentrated, and diisopropyl ether (4500 mL) and water were added. The aqueous layer was neutralized with 1M hydrochloric acid, and partitioned and extracted with ethyl acetate. The organic layer was washed with 25% brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residual crude crystals were recrystallized from a mixed solvent of diisopropyl ether and hexane to give the title compound (240 g) as pale-yellow crystals.

1. concentrationThe mixture was concentrated
2. additiondiisopropyl ether (4500 mL) and water were added
3. custompartitioned
4. extractionextracted with ethyl acetate
5. washThe organic layer was washed with 25% brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated under reduced pressure
8. customthe residual crude crystals were recrystallized from a mixed solvent of diisopropyl ether and hexane

ORD record

ord-f69d2b54a0f14b17b43820f2d9b160a4

Source dataset

uspto-grants-2012_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08114902B2