Water → 2-(4-Bromo-2-methoxyphenyl)acetic acid
Reaction equation
[OH-:1].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([O:13][CH3:14])[CH:5]=1.[OH2:15]>CO>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:15])=[O:1])=[C:6]([O:13][CH3:14])[CH:5]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
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.