Ethane, 1-fluoro-2-iodo- → rac-2-[(Diphenylmethylene)amino]-4-fluorobutanonitrile

Participants

Reaction Conditions

Reaction Steps

16.5 g (74.91 mmol) of [(diphenylmethylene)amino]acetonitrile were initially charged in 495 ml of abs. THF, and 35.96 ml (89.89 mmol) of n-butyllithium (2.5 N in hexane) were added at −78° C. under argon, and the mixture was stirred at −78° C. for 15 min. Subsequently, the reaction solution was warmed up to 0° C. 13.03 g (74.91 mmol) of 1-iodo-2-fluoroethane were added dropwise to the reaction solution, which was stirred at 0° C. for a further 15 min. The reaction solution was quenched with water at 0° C., ethyl acetate was added and the mixture was washed with saturated aqueous sodium chloride solution. The aqueous phase was reextracted twice with ethyl acetate. The combined organic phases were dried over sodium sulphate, filtered and concentrated by rotary evaporation. The residue was purified by means of silica gel chromatography (eluent:dichloromethane/cyclohexane=1/1 to 2/1). 18.7 g of the target compound were obtained (80% of theory, 85% purity).

Provenance & Evidence