Sodium Cyanide → [1-(4-Bromophenyl)-cyclopentyl]-acetonitrile

Temperatur

140 °C

To a stirred solution of methanesulfonic acid 1-(4-bromophenyl)-cyclopentylmethyl ester (227) (20 g, 60.01 mmol) in dimethyl sulfoxide (100 mL) were added KI (0.99 g, 6.00 mmol) and NaCN (4.41 g, 90.02 mmol). The reaction mixture was then stirred at 140° C. for 5 h. After completion of the reaction, the reaction mixture was diluted with water, extracted with ethyl acetate (2×250 mL) and the organic layer was washed with water and brine. It was then dried over Na2SO4, and concentrated. The crude product was purified by 100-200 silica column chromatography using 5% ethyl acetate in hexane as the eluent to give [1-(4-bromophenyl)-cyclopentyl]-acetonitrile (228) (13.9 g, 87%) as a colorless thick liquid.

1. customAfter completion of the reaction
2. extractionextracted with ethyl acetate (2×250 mL)
3. washthe organic layer was washed with water and brine
4. dry with materialIt was then dried over Na2SO4
5. concentrationconcentrated
6. customThe crude product was purified by 100-200 silica column chromatography

ORD-Eintrag

ord-a731bf4a9c0d4741b14e384748a5e865

Quelldatensatz

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09045486B2