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

A solution of NaOH (5.72 g, 143 mmol) in water (29 mL) was added to a solution of (4-bromo-2-methoxy-phenyl)-acetonitrile (10.2 g, 45.1 mmol) in MeOH (100 mL). The reaction mixture was heated at reflux for 18 hours. The solvent was evaporated under reduced pressure and water was added. The aqueous mixture was washed with diethyl ether, and the aqueous layer was acidified by addition of aqueous HCl (2 M) to pH 1. The aqueous mixture was then extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered, and evaporated under reduced pressure to give 9.49 g (86% yield) of (4-bromo-2-methoxy-phenyl)-acetic acid.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 18 hours
3. customThe solvent was evaporated under reduced pressure and water
4. additionwas added
5. washThe aqueous mixture was washed with diethyl ether
6. additionthe aqueous layer was acidified by addition of aqueous HCl (2 M) to pH 1
7. extractionThe aqueous mixture was then extracted with EtOAc
8. washthe combined organic extracts were washed with brine
9. dry with materialdried over Na2SO4
10. filtrationfiltered
11. customevaporated under reduced pressure

ORD record

ord-867923fd76754b66a589cad80ca3686d

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07776910B2