Water → 4-Bromo-3-(methoxymethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate (Intermediate 28, step 2), (7 g; 27.02 mmol) in EtOH (210 mL) was added NaOH (16.21 mL; 5 M; 81.05 mmol). The resulting reaction mixture was heated at 60° C. for one hour. It was then cooled to RT and concentrated under vacuum to give a yellow solid. Water was added and the aqueous phase was washed with EtOAc. The aqueous phase was then acidified with HCl (1 M) and extracted with EtOAc. Organic phase was dried over MgSO4, filtered and concentrated under vacuum to give the title compound as a yellow solid (5.81 g, 87%). 1H NMR (DMSO-d6, 300 MHz) 13.19 (br s, 1H), 8 (m, 1H), 7.77-7.76 (m, 2H), 4.49 (s, 2H), 3.40 (s, 3H). LC/MS (Method B): 245.0 (M−H)−. HPLC (Method A) Rt 3.63 min (purity: 97.4%).

Provenance & Evidence