Hydrochloric Acid → HCID 59689163, compound

Participants

Reaction Steps

A suspension of 5 mmol magnesium-turnings in 10 ml diethyl ether was treated with 5 mmol 4-bromobenzotrifluoride to form the corresponding Grignard-reagent. This reagent was slowly added to a cooled solution of 5 mmol 4-(trifluoromethyl)benzonitrile in 10 ml of tetrahydrofuran at −70° C. After 1 hour at −70° C., the reaction mixture was stirred additional 2 hours at room temperature and then refluxed overnight. The resulting mixture was cooled again to 0° C. and diluted with 10 ml of methanol and 10 mmol sodium borohydride were added. After stirring for 2 hours at room temperature, the mixture was poured into 100 ml of 0.5 M aqueous hydrochloric acid and extracted with diethyl ether. The aqueous phase was adjusted to pH=10 by addition of diluted aqueous sodium hydroxide and extracted 3 times with dichloromethane. Chromatography (SiO2; dichloromethane/methanol) yielded the title compound as a slightly brown foam.

Provenance & Evidence