Formamide → HCID 22313804, Verbindung

To a stirred solution of phosphorus pentasulfide (4.0 g, 9.0 mmol) in dioxane 40 ml) was added formamide (4.8 g, 106 mmol), and the mixture was heated at reflux temperature for 2 hours. The reaction mixture was cooled down to room temperature, and the solution was decanted away from solids. To a stirred solution of 2-bromo-1-(2-fluoro-4-hydroxyphenyl)-1-ethanone (1.2 g, 5.15 mmol) in dioxane (14 ml) was added the thioformamide solution, and the mixture was heated at reflux temperature for 6 hours. The reaction mixture was cooled down to room temperature, and made basic by addition of 2N NaOH aqueous solution. The whole was extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by flash chromatography eluting with ethyl acetate-hexane (1:4) to give title compound (864 mg, 86% yield).

1. temperaturethe mixture was heated
2. temperatureat reflux temperature for 2 hours
3. customthe solution was decanted away from solids
4. temperaturethe mixture was heated
5. temperatureat reflux temperature for 6 hours
6. temperatureThe reaction mixture was cooled down to room temperature
7. extractionThe whole was extracted with ethyl acetate
8. washThe organic layer was washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated in vacuo
11. customThe residue was purified by flash chromatography
12. washeluting with ethyl acetate-hexane (1:4)

ORD-Eintrag

ord-80b10adfd2c048418193c26bc123894b

Quelldatensatz

uspto-grants-2004_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06727238B2