Dimethylformamide → HCID 22996197, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3,5-bis-methoxymethyl-benzene (522 mg, 2.130 mmol) in dimethylformamide (5 mL) at room temperature was added zinc cyanide (150 mg, 1.278 mmol). The reaction mixture was degassed by passing argon through for I h before tetrakis(triphenylphosphine)palladium (148 mg, 0.128 mmol) was added. The reaction mixture was heated at 80° C. under argon for 12 h. The reaction mixture was taken up in toluene (30 mL) and washed with 10% ammonium hydroxide (2×40 mL), brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 20% ethyl acetate in hexanes yielded 3,5-bis-methoxymethyl-benzonitrile (320 g, 79%).

Provenance & Evidence