5-Bromo-1-indanone → 1-oxo-2,3-dihydro-1H-indene-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture 5-bromo-indan-1-one (1 g, 4.7 mmol), zinc cyanide (1.11 g, 9.4 mmol) in NMP/THF (2 mL/4 mL) in a sealed tube, is added palladium bis(tri-t-butyl-phosphine) (120 mg, 5% mmol). The mixture is purged with N2 and heated at 120° C. for 3 h. Then the reaction mixture is cooled to rt, diluted with H2O, and extracted with EtOAc (3×20 mL). The combined organic phases are washed with saturated ammonium chloride aqueous solution and brine and dried over Na2SO4. The crude product obtained after concentration is purified by silica gel column chromatography with mixed solvent hexanes/EtOAc (5/1-3/1) to afford 1-oxo-indan-5-carbonitrile as a light yellow solid: ESMS m/z 158.0 (M+H+).

Provenance & Evidence