Formamide → 2-Fluoro-4-(thiazol-4-yl)phenol

To a stirred solution of phosphorus pentasulfide (8.6 g, 19.3 mmol) in dioxane (53 ml) was added formamide (5.2 g, 115.5 mmol), and the mixture was heated at reflux temperature for 2 hours. The mixture was cooled down to room temperature, and the solution was decanted away from solids. To a stirred solution of 2-bromo-1-(3-fluoro-4-hydroxyphenyl)-1-ethanone (3.02 g, 12.98 mmol) in dioxane (50 ml) was added the thioformamide solution, and the mixture was heated at reflux temperature for 6 hours. The mixture was cooled down to room temperature, and made basic by addition of 0.5M 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 (1:3) to give title compound (2.11 g, 83% 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 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 (1:3)

ORD record

ord-b715ebddeb2347c0afb4846d30c2d4ab

Source dataset

uspto-grants-2005_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06949536B2