Diethyl Ether → 2-(3-Chloro-5-methylphenyl)acetonitrile

To a flask equipped with additional funnel, was placed potassium cyanide (29.6 g, 0.45 mol) and distilled water (55 ml). The mixture was heated up to 70° C. in an oil bath. With stirring, 1-Bromomethyl-3-chloro-5-methyl-benzene (46) (35 g, 0.16 mol) in ethanol (180 ml) was then dropwise added over 1 hr through the addition funnel. After completion of addition, the mixture was refluxed for 8 hr. After cooling to room temperature, ether was added to the mixture. The mixture was washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:9)) to afford 20 g (77%) of a pale brown oil. 1H NMR (200 MHz, CDCl3) δ: 2.31 (3H, s), 3.66 (2H, s), 7.02 (1H, s), 7.09 (2H, s).

1. customTo a flask equipped with additional funnel
2. distillationdistilled water (55 ml)
3. additionAfter completion of addition
4. temperaturethe mixture was refluxed for 8 hr
5. temperatureAfter cooling to room temperature
6. washThe mixture was washed with water
7. dry with materialdried with anhydrous magnesium sulfate
8. filtrationfiltered
9. customevaporated in vacuo
10. customthe residue was purified by silica gel column chromatography (eluent, ether:hexane (1:9))

ORD-Eintrag

ord-0309f364da8d4e2d833f1ec431fceb10

Quelldatensatz

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08106064B2