Dimethylformamide → 2-Chlorocyclohex-1-ene-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Phosphorus oxychloride (11.5 mL; 124 mmol) was cooled in an ice-salt bath and DMF (10.0 mL; 130 mmol) was added over a period of 20 min (a sticky white solid was formed). Cyclohexanone (8.0 mL; 77 mmol) was added over 15 min (the sticky solid turned into a bright yellow solution). The mixture was heated at 50° C. and hydroxylamine hydrochloride (30 g; 432 mmol) was added in 5 portions at 5 min intervals maintaining the temperature between 45 and 55° C. via cooling if needed. The reaction mixture was poured into ice-water (300 mL) and the aqueous mixture was stirred for 1 h. The brown solid was filtered, washed with water and dried under reduced pressure over phosphorus pentoxide to afford 9.06 g (83%) of 2-chlorocyclohex-1-enecarbonitrile as a rust-brown solid. ESI/APCI (+): 160-162 (M+H+H2O). 1H-NMR (400 MHz, DMSO-d6) (ppm) δ: 2.48 (2H, m); 2.35 (2H, m), 1.74-1.77 (2H, M), 1.71-1.66 (2H, M).

Provenance & Evidence