Aniline → 2-Fluoro-6-(phenylamino)benzonitrile

Aniline (4.66 g, 50 mmol) was dissolved in dimethyl sulfoxide (20 mL) and stirred under argon at room temperature. Sodium hydride, dry, 95% (1.51 g, 60 mmol) was added in portions and a deep purple color developed while the mixture was stirred at room temperature for 1 hour. The mixture was cooled to 0° C. in an ice bath and 2,6-difluorobenzonitrile (7.15 g, 50 mmol) dissolved in dimethyl sulfoxide (5 mL) was added and the mixture stirred at room temperature for 1.5 hours. The reaction mixture was partitioned between ethyl acetate and water, and the organic phase was washed with water (5×), brine (1×) dried over anhydrous Na2SO4 filtered, and evaporated to give the crude product which was then chromatographed on silica gel eluted with 0–25% CH2Cl2 in hexane to give the title compound as a white amorphous solid. ES (+) MS m/e=213 (MH+).

1. dry with materialSodium hydride, dry
2. addition95% (1.51 g, 60 mmol) was added in portions
3. stirringwas stirred at room temperature for 1 hour
4. temperatureThe mixture was cooled to 0° C. in an ice bath
5. additionwas added
6. stirringthe mixture stirred at room temperature for 1.5 hours
7. customThe reaction mixture was partitioned between ethyl acetate and water
8. washthe organic phase was washed with water (5×), brine (1×)
9. dry with materialdried over anhydrous Na2SO4
10. filtrationfiltered
11. customevaporated
12. customto give the crude product which
13. customwas then chromatographed on silica gel
14. washeluted with 0–25% CH2Cl2 in hexane

ORDレコード

ord-0ad13eb89e4d465fa918ed7692c4f9ab

出典データセット

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07053099B1