Hydrochloric Acid → Benzenepropanal, 5-fluoro-2-methoxy-

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl-3-(5′-fluoro-2′-methoxyphenyl)propionate (5.8 g, 25.7 mmol) in dry toluene (40 mL) under Ar was added DIBAL solution (1 M in toluene, 30 mL, 30 mmol) at −78° C. The reaction was stirred at this temperature for 2 h. Methanol (2 mL) was added to the reaction mixture and the reaction was allowed to warm to 0° C. The reaction mixture was then poured into a separatory funnel containing HCl solution (1 N, 150 mL). The organic function was extracted with ethyl acetate (3×100 mL) and the combined organic layers were washed with brine (80 mL) and dried over sodium sulfate. The crude product that was obtained after removal of the solvent in vacuo was purified by flash column chromatography (20% EtOAc in hexane, Rf=0.20) to give the product (3.1 g, 66%).

Provenance & Evidence