Hydrochloric Acid → 3-Chloro-5-methoxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

3,5-Dichlorobenzonitrile (52.93 g, 307.7 mmol) was dissolved in anhydrous DMF (300 mL) and cooled to 0° C. in an ice bath. Sodium methoxide (18.28 g, 338.5 mmol) was added as a solid and the mixture was allowed to warm to RT and stirred overnight. The reaction mixture was poured into a mixture of 10% HCl and ice. The solid that formed was filtered, washed with water, and dried overnight. The solid was dissolved in EtOAc and DCM and filtered to remove insoluble material. The solution was washed with water, dried over MgSO4, filtered and evaporated to afford the title compound (46.48 g, 90%) as a solid. 1H NMR (400 MHz, CDCl3): δ ppm 7.20 (t, 1H), 7.10 (t, 1H), 7.03 (dd, 1H), 3.82 (s, 3H).

Provenance & Evidence