Hydrochloric Acid → 4-Fluorobenzamidine

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of hexamethyldisilazane (7 mL) in Et2O (40 mL) was added n-BuLi (1.6M in hexanes, 20.6 mL), followed by a solution of 4-fluorobenzonitrile (2 g) in Et2O (10 ml). After stirring at 0° C. for 10 min, the mixture was allowed to warm to RT and was stirred at RT for 20 h. The mixture was acidified to pH 1 by adding a 1M HCl solution and was washed with CHCl3. The aq. layer was then basified to pH 14 by adding Na2CO3 and NaOH and was extracted twice with CHCl3. The org. layers were dried (Na2SO4) and evaporated off to afford the desired compound (1.59 g).

Provenance & Evidence