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

Temperature

120 °C

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+).

1. customThe mixture is purged with N2
2. temperatureThen the reaction mixture is cooled to rt
3. additiondiluted with H2O
4. extractionextracted with EtOAc (3×20 mL)
5. washThe combined organic phases are washed with saturated ammonium chloride aqueous solution and brine
6. dry with materialdried over Na2SO4
7. customThe crude product obtained
8. concentrationafter concentration
9. customis purified by silica gel column chromatography with mixed solvent hexanes/EtOAc (5/1-3/1)

ORD record

ord-283436d4dbfa4aa8a8baaa92ecb4468f

Source dataset

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08153671B2