Dimethylformamide → HCID 131724068, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-benzene (2.05 g, 4.601 mmol, example 35) in dimethylformamide (8 mL) at room temperature was added zinc cyanide (324 mg, 2.761 mmol). The reaction mixture was degassed by passing argon through for 1 h before tetrakis(triphenylphosphine)palladium (319 mg, 0.276 mmol) was added. The reaction mixture was heated at 80° C. under argon for 12 h. The reaction mixture was taken up in toluene (40 mL) and washed with 2 N 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 5% ethyl acetate in hexanes yielded 3,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-benzonitrile (1.47 g, 82%).

Provenance & Evidence