Hydrochloric Acid → 4-amino-2-(trifluoromethoxy)benzonitrile

1,1-Dimethylethyl {4-bromo-3-[(trifluoromethyl)oxy]phenyl}carbamate (Intermediate 50, 1.0 g, 2.8 mmol) was dissolved in dry DMF (25 mL). To this solution was added CuCN (1.0 g, 11.1 mmol), and the reaction mixture was heated to reflux for 5 h. A second portion of CuCN (500 mg, 5.6 mmol) was added and heating at reflux was continued for 10 h. The reaction mixture was cooled to room temperature, and FeCl3 was added. This was followed by 1N HCl at 0° C. and the mixture was stirred for 2 hr at room temperature. The reaction mixture was diluted with water and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude product. This was purified by column chromatography (60-120 silica gel), eluting with 30% ethyl acetate/pet ether to give the title compound (260 mg).

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for 5 h
3. temperatureheating
4. temperatureat reflux
5. extractionextracted with ethyl acetate (2×50 mL)
6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure
8. customto afford the crude product
9. customThis was purified by column chromatography (60-120 silica gel)
10. washeluting with 30% ethyl acetate/pet ether

ORDレコード

ord-cac58483c3a441abadcd7d3c27bcd883

出典データセット

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09115132B2