Dimethyl Sulfoxide → Ethyl (2-fluoro-3-methylphenyl)acetate

Temperatur

60 °C

A mixture of 2-fluoro-3-methylbenzyl bromide (2.0 g), sodium cyanide (2.41 g), sodium iodide (148 mg) and DMSO (10 ml) was stirred at 60° C. for two hours. Water and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with brine. The resulting organic layer was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. 5 N hydrochloric acid (15 ml) was added to the residue, and the reaction solution was heated at 110° C. for 22 hours. The reaction solution was brought to room temperature. Chloroform was added and the organic layer was separated. The organic layer was concentrated under reduced pressure. Saturated hydrogen chloride-ethanol (15 ml) was added to the residue, and the reaction solution was stirred at 85° C. for four hours. The reaction solution was concentrated under reduced pressure, and then diluted with ethyl acetate and washed with saturated sodium bicarbonate water and then with brine. The resulting organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain the title compound (1.1 g). The property values of the compound are as follows.

1. customthe organic layer was separated
2. washThe organic layer was washed with brine
3. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
4. concentrationThe organic layer was concentrated under reduced pressure
5. addition5 N hydrochloric acid (15 ml) was added to the residue
6. temperaturethe reaction solution was heated at 110° C. for 22 hours
7. customwas brought to room temperature
8. additionChloroform was added
9. customthe organic layer was separated
10. concentrationThe organic layer was concentrated under reduced pressure
11. additionSaturated hydrogen chloride-ethanol (15 ml) was added to the residue
12. stirringthe reaction solution was stirred at 85° C. for four hours
13. concentrationThe reaction solution was concentrated under reduced pressure
14. additiondiluted with ethyl acetate
15. washwashed with saturated sodium bicarbonate water
16. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
17. concentrationconcentrated under reduced pressure

ORD-Eintrag

ord-761e8e3a9c9744d3a9e703a7e319a9f4

Quelldatensatz

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07935815B2