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

HRID 426123Notes

Reaction equation

[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.CCOCC>C(O)C>[Cl:13][C:8]1[CH:7]=[C:6]([CH2:5][C:1]#[N:2])[CH:11]=[C:10]([CH3:12])[CH:9]=1

Participants

Conditions

Temperature: 70 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-0309f364da8d4e2d833f1ec431fceb10
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106064B2

Reaction notes

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