Hydrochloric Acid → HCID 86660263, compound

Participants

Reaction Conditions

Reaction Steps

1-Bromo-3-difluoromethoxy-6-methylaniline (1.70 g, 6.74 mmol) is initially charged in 7 ml of DMF, and copper(I) cyanide (0.79 g, 8.76 mmol) is added. The reaction is stirred at 150° C. overnight. After cooling to room temperature, the DMF is removed under reduced pressure and 15 ml of water and ethylenediamine (3.6 ml, 53.9 mmol) are added to the residue. The mixture is then stirred at room temperature for 1 hour. The reaction mixture is then acidified to pH=5 using hydrochloric acid, and the aqueous phase is extracted with ethyl acetate (6 times). The combined organic phases are dried over sodium sulphate and then purified chromatographically on silica gel. (logP: 1.90; MH+: 199, 1H-NMR (400 MHz, DMSO, ppm): 2.12 (s, 3H), 5.91, (s, 2H), 7.10 (t, 1H), 7.20 (m, 2H).

Provenance & Evidence