Sodium Acetate → Methyl 3-(acetoxymethyl)-4-bromobenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-bromo-3-(bromomethyl)benzoate (Intermediate 1 Step 1, 6.5 g, 21 mmol) in AcOH (32.5 mL) was added sodium acetate (3.46 g, 42 mmol) and the reaction mixture was stirred at 100° C. for 15 hours. After concentration in vacuo, the residue was partitioned between EtOAc and water. The organic layer was washed with a 5% aqueous solution of NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. Purification by chromatography (silica, chex/EtOAc) afforded the title compound as a white solid (4.78 g, 79%). 1H NMR (DMSO-d6) δ 8.03 (m, 1H), 7.85 (m, 2H), 5.18 (s, 2H), 3.87 (s, 3H), 2.11 (s, 3H). HPLC (Method A) Rt 4.37 min (purity 98.1%).

Provenance & Evidence