Hydrochloric Acid → 4-(5-Fluoro-2-methoxyphenyl)butanal

Temperature

0 °C

To a solution of ethyl-4-(5′-fluoro-2′-methoxyphenyl)butyrate (2.25 g, 9.4 mmol) in dry toluene (30 mL) under Ar(g) was added DIBAL solution (1 M in toluene, 11 mL, 11 mmol) at −78° C. Then the reaction was stirred at this temperature for 2 h. Methanol (2 mL) was then added to the reaction mixture and the reaction was allowed to warm to 0° C. The reaction mixture was poured into a separatory funnel containing HCl solution (1 N, 100 mL). The organic function was extracted with ethyl acetate (3×60 mL) and the combined organic layers were washed with brine (80 mL) and dried over sodium sulfate. The crude product that obtained by removal of the solvent in vacuo was purified by flash column chromatography (10% EtOAc in hexane, Rf=0.10) to give the product (1.30 g, 70%).

1. additionThe reaction mixture was poured into a separatory funnel
2. extractionThe organic function was extracted with ethyl acetate (3×60 mL)
3. washthe combined organic layers were washed with brine (80 mL)
4. dry with materialdried over sodium sulfate
5. customThe crude product that obtained by removal of the solvent in vacuo
6. customwas purified by flash column chromatography (10% EtOAc in hexane, Rf=0.10)

ORD record

ord-dc67383be119405b94455fe3cf2e4fba

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08168635B2