Diethyl Ether → 2,6-Difluoro-N,N-di(propan-2-yl)benzene-1-carboximidamide

Participants

Reaction Conditions

Reaction Steps

A solution of EtMgBr in ether (8.0 mL, 3.0 M, 24 mmol) was added to a solution of diisopropylamine (2.50 g, 24.8 mmol) in toluene (60 mL) at 50° C. The mixture was stirred for 1 h and a white precipitate formed. Next, the mixture was cooled to 0° C. and 2,6-difluorobenzonitrile (3.34 g, 24 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 16 h subsequently. The conversion, determined by GC, appeared to be 98%. The mixture was quenched with an aqueous NH4Cl solution (1%, 100 mL). The organic phase was separated from the aqueous phase and the latter was extracted with diethylether (200 mL) twice. The combined organic phases were dried over Na2SO4, filtered and the solvents were removed under reduced pressure giving 5.40 g (91%) of pure product. The ligand was characterized by 1H NMR (300 MHz) (CDCl3) δ (ppm): 7.2 (m, 1H), 6.8 (m, 2H), 5.5 (bs, 1H), 3.7 (bs, 1H), 3.4 (bs, 1H), 1.5 (bs, 6H), 1.0 (bs, 6H), by 13C NMR 75 MHz (CDCl3) δ (ppm): 158.9 (dd, J=248 Hz, J=8 Hz), 155.7, 130.1, 130.0, 129.8, 112.1, 112.0, 111.9, 111.852.0 (bs), 46.2 (bs), 21.3, 20.5 and by 19F (282 MHz) (CDCl3) δ (ppm) −114.

Provenance & Evidence