Phosphorus oxychloride → 6-Chloro-4-(trifluoromethyl)nicotinonitrile

温度

60 °C

A mixture of 6-chloro-4-(trifluoromethyl)nicotinamide (0.847 g, 3.77 mmol, Preparation #27) and POCl3 (7.03 mL, 75.0 mmol) was heated at about 60° C. with stirring for about 1 h. The reaction mixture was cooled to ambient temperature and concentrated to dryness under reduced pressure and the resulting material was partitioned between chilled saturated aqueous NaHCO3 (30 mL) and EtOAc (30 mL). The layers were separated and the organic solution was washed with saturated aqueous NaHCO3 solution (30 mL) and brine (30 mL), dried over anhydrous Na2SO4, filtered, and concentrated to dryness under reduced pressure to give 6-chloro-4-(trifluoromethyl)nicotinonitrile (0.67 g, 86%) as a brown liquid: LC/MS (Table 2, Method a) Rt=2.31 min: 1H NMR (CDCl3) δ 8.87 (s, 1H), 7.75 (s, 1H).

1. temperatureThe reaction mixture was cooled to ambient temperature
2. concentrationconcentrated to dryness under reduced pressure
3. customthe resulting material was partitioned
4. temperaturebetween chilled saturated aqueous NaHCO3 (30 mL) and EtOAc (30 mL)
5. customThe layers were separated
6. washthe organic solution was washed with saturated aqueous NaHCO3 solution (30 mL) and brine (30 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated to dryness under reduced pressure

ORDレコード

ord-91d7806ae9c14584a83f66c821bc64aa

出典データセット

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08962629B2