Hydrochloric Acid → Benzyl 3-fluoro-4-formylbenzoate

Participants

Reaction Steps

60% NaH (0.23 mol) is added portionwise to a solution of 3-fluoro-4-formyl benzoic acid (3, 0.19 mol) in dry dimethylformamide (DMF) (570 mL). The mixture is stirred at room temperature for 45 min. Benzyl bromide (0.23 mol) is added dropwise to the mixture. After stirring at room temperature for 5 h, the reaction mixture is poured into 1N HCl (ca. 1000 mL) and extracted twice with EtOAc. The combined extracts are washed with saturated aqueous NaHCO3, brine, dried over MgSO4, and evaporated in vacuo to give crude 3-fluoro-4-formyl benzoic acid benzyl ester (6).

Provenance & Evidence