p-Fluoronitrobenzene → HCID 54428535, compound

Participants

Reaction Steps

A suspension of 15.0 gm (82 mMol) potassium hydride (22% dispersion in mineral oil) in 10 mL tetrahydrofuran was cooled in an ice bath. To this suspension was slowly added a solution of 9.8 gm (68 mMol) N,N-dimethyl-5-amino-2-pentanone oxime in 20 mL tetrahydrofuran resulting in vigorous gas evolution. Once this addition was complete, a solution of 12.5 gm (88.3 mMol) 4-nitrofluorobenzene and 0.90 gm (3.4 mMol) 18-crown-6 in 10 mL tetrahydrofuran were added. The dark solution was stirred for 1 hour at ice bath temperature and then for 3 hours at room temperature. The reaction mixture was then poured into 100 mL of aqueous 5% potassium carbonate and the resulting mixture was extracted with dichloromethane. These organic extracts were combined, washed with aqueous 5% potassium carbonate, dried over sodium sulfate and concentrated under reduced pressure. The residual oil was subjected to flash silica gel chromatography, eluting with 10% methanol in dichloromethane. Fractions containing product were combined and concentrated under reduced pressure to provide 7.3 gm (40%) of the desired oxime ether as a dark oil.

Provenance & Evidence