Lithium iodide → 3-Chloro-5-hydroxybenzonitrile

Participants

Reaction Conditions

Reaction Steps

A 250 mL round bottom flask was charged 3-chloro-5-methoxybenzonitrile (4.2 g; 25.05 mmol) and 2,4,6-collidine (60 mL) was added. The mixture was stirred under an argon atmosphere until the solution was homogeneous. Anhydrous lithium iodide (10.06 g; 75.18 mmol) was added and the mixture was heated to 175° C. for 3 h. The reaction mixture was cooled to RT and partitioned between 10% HCl and EtOAc. The EtOAc phase was washed sequentially with 10% HCl and brine, dried (Na2SO4), filtered and evaporated in vacuo to afford a oil which was crystallized from hexanes to afford 3-chloro-5-hydroxybenzonitrile (130c, 3.5 g, 91% theory).

Provenance & Evidence