Ethanol → 4-bromo-3-ethoxymethyl-benzoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-bromo-3-(bromomethyl)benzoate (Intermediate 28, Step 1), (2.50 g; 8.12 mmol; 1 eq.) in EtOH (12.50 mL) was added sodium ethylate (1 104.83 mg; 16.24 mmol; 2 eq.) and the mixture was stirred overnight at 80° C. After evaporation of the solvent, the mixture was partitioned between EtOAc and water. The organic layer was washed with a 5% NaHCO3 aqueous solution, NaCl sat. solution, dried over magnesium sulfate, filtered off and dried under vacuum to afford a yellow oil. Purification by flash chromatography (cHex/ethyle acetate) afforded the title compound as a yellow oil. 1H NMR (CDCl3) δ 8.13 (d, J=2.1 Hz, 1H), 7.80 (dd, J=8.3, 2.1 Hz, 1H), 7.61 (d, J=8.3 Hz, 1H), 4.58 (s, 2H), 4.38 (q, J=7.2 Hz, 2H), 3.64 (q, J=7.0 Hz, 2H), 1.39 (t, J=7.2 Hz, 3H), 1.30 (t, J=7.0 Hz, 3H). LC/MS (Method B): 382.2 ((M−H)+ACN)−; 330.2 ((M+H)+ACN)+. HPLC (Method A), Rt 4.90 min (purity: 78.5%).

Provenance & Evidence