2-Chloroethanol → 2-Fluoro-3-(2-hydroxyethoxy)-5-methoxybenzaldehyde

Temperature

100 °C

Under nitrogen atmosphere, a mixture of 2-fluoro-3-hydroxy-5-methoxybenzaldehyde (17.01 g, 100 mmol), 2-chloroethanol (8.72 mL, 130 mmol), sodium iodide (19.49 g, 130 mmol), potassium carbonate (17.97 g, 130 mmol), and N,N-dimethylformamide (85 mL) was stirred at 100° C. for 4.25 hours, after which 2-chloroethanol (4.70 mL, 70 mmol), sodium iodide (10.49 g, 70 mmol), potassium carbonate (9.68 g, 70 mmol), and N,N-dimethylformamide (17 mL) were added thereto, and the resulting mixture was stirred at the same temperature for 4.25 hours. To the mixture, 2-chloroethanol (2.01 mL, 30 mmol), sodium iodide (4.50 g, 30 mmol), and potassium carbonate (4.15 g, 30 mmol) were added, and the resulting mixture was stirred at 100° C. for 7 hours, after which 2-chloroethanol (2.01 mL, 30 mmol) was added thereto, and the resulting mixture was stirred at the same temperature for 2.5 hours. After cooling the mixture, ethyl acetate and water were added to the reaction mixture, and the resulting mixture was extracted. The organic layer was washed with water and concentrated under reduced pressure to obtain a crude product containing the captioned compound (17.70 g) as a red-brown solid.

1. stirringthe resulting mixture was stirred at the same temperature for 4.25 hours
2. stirringthe resulting mixture was stirred at 100° C. for 7 hours
3. stirringthe resulting mixture was stirred at the same temperature for 2.5 hours
4. additionwere added to the reaction mixture
5. extractionthe resulting mixture was extracted
6. washThe organic layer was washed with water
7. concentrationconcentrated under reduced pressure

ORD record

ord-2125abc69cb24bdfa74486aee9ad507f

Source dataset

uspto-grants-2013_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08436009B2